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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:34 UTC

Update Date

2019-07-23 07:15:28 UTC

HMDB ID

HMDB0060959

Secondary Accession Numbers

HMDB60959

Metabolite Identification

Common Name

4'-N-desmethylolanzapine

Description

4'-N-desmethylolanzapine 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

HMDB0060959
     RDKit          3D
4'-N-desmethylolanzapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7461    4.7853   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970    3.3327   -0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2619    2.2452   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    1.0335   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800    0.9769    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    2.6211    0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.1411    0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.5314    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -2.2764   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -3.6361   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -4.1948   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -3.4264   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.0515   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.4272   -0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0265   -0.1903   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.0024   -0.0378 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.0300    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460   -0.5427    1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -0.2541   -0.1393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.6781   -0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284    0.1586   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    5.2112    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613    5.2631   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    4.8584   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    2.4288   -0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.1165    0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091   -1.8003    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -4.2725   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616   -5.2730   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -3.8386   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    1.0616    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.5856    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -0.0785    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.6279    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1066   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275    1.6945   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    0.7574   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547    0.8550   -1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -0.8506   -1.7528 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
  5  7  1  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6  2  1  0
 13  8  1  0
 21 16  1  0
 15  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
M  END


  Mrv0541 07091309092D          

 21 24  0  0  0  0            999 V2000
   -2.0524    0.7689    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
   -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
   -0.7035   -2.9896    0.0000 N   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
    0.0289   -1.5111    0.0000 N   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
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  2  0  0  0  0
 14  5  2  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 12  2  0  0  0  0
 17  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060959

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCNCC2)S1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N4S/c1-11-10-12-15(20-8-6-17-7-9-20)18-13-4-2-3-5-14(13)19-16(12)21-11/h2-5,10,17,19H,6-9H2,1H3

> <INCHI_KEY>
FHPIXVHJEIZKJW-UHFFFAOYSA-N

> <FORMULA>
C16H18N4S

> <MOLECULAR_WEIGHT>
298.406

> <EXACT_MASS>
298.125217286

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.00287404788987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.005447144666667

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.174482278344204

> <JCHEM_PKA_STRONGEST_BASIC>
8.825951859466409

> <JCHEM_POLAR_SURFACE_AREA>
39.660000000000004

> <JCHEM_REFRACTIVITY>
88.57900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060959
     RDKit          3D
4'-N-desmethylolanzapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7461    4.7853   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970    3.3327   -0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2619    2.2452   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    1.0335   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800    0.9769    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    2.6211    0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.1411    0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.5314    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -2.2764   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -3.6361   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -4.1948   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -3.4264   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.0515   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.4272   -0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0265   -0.1903   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.0024   -0.0378 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.0300    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460   -0.5427    1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -0.2541   -0.1393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.6781   -0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284    0.1586   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    5.2112    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613    5.2631   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    4.8584   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    2.4288   -0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.1165    0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091   -1.8003    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -4.2725   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616   -5.2730   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -3.8386   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    1.0616    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.5856    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -0.0785    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.6279    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1066   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275    1.6945   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    0.7574   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547    0.8550   -1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -0.8506   -1.7528 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
  5  7  1  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6  2  1  0
 13  8  1  0
 21 16  1  0
 15  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  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      -3.831   1.435   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      -2.334   1.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.209  -0.226   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.251  -0.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.925   1.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.738  -1.441   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.150   1.271   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.313  -5.581   0.000  0.00  0.00           N+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       0.054  -2.821   0.000  0.00  0.00           N+0
HETATM   21  S   UNK     0      -1.163   2.076   0.000  0.00  0.00           S+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   14                                                       
CONECT    6    8   17                                                       
CONECT    7    9   17                                                       
CONECT    8    6   20                                                       
CONECT    9    7   20                                                       
CONECT   10   11   12                                                       
CONECT   11    1   10   21                                                  
CONECT   12   10   15   16                                                  
CONECT   13    4   14   18                                                  
CONECT   14    5   13   19                                                  
CONECT   15   12   18   20                                                  
CONECT   16   12   19   21                                                  
CONECT   17    6    7                                                       
CONECT   18   13   15                                                       
CONECT   19   14   16                                                       
CONECT   20    8    9   15                                                  
CONECT   21   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0060959
HETATM    1  C1  UNL     1      -0.746   4.785  -0.224  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.097   3.333  -0.121  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.262   2.245  -0.152  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.821   1.034  -0.040  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.180   0.977   0.097  1.00  0.00           C  
HETATM    6  S1  UNL     1      -2.634   2.621   0.064  1.00  0.00           S  
HETATM    7  N1  UNL     1      -3.083  -0.141   0.239  1.00  0.00           N  
HETATM    8  C6  UNL     1      -2.824  -1.531   0.005  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.958  -2.276  -0.056  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.799  -3.636  -0.281  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.550  -4.195  -0.435  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.434  -3.426  -0.369  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.555  -2.051  -0.143  1.00  0.00           C  
HETATM   14  N2  UNL     1      -0.304  -1.427  -0.107  1.00  0.00           N  
HETATM   15  C12 UNL     1       0.027  -0.190  -0.064  1.00  0.00           C  
HETATM   16  N3  UNL     1       1.429  -0.002  -0.038  1.00  0.00           N  
HETATM   17  C13 UNL     1       2.153   0.030   1.193  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.546  -0.543   1.092  1.00  0.00           C  
HETATM   19  N4  UNL     1       4.200  -0.254  -0.139  1.00  0.00           N  
HETATM   20  C15 UNL     1       3.502   0.678  -0.982  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.128   0.159  -1.288  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.802   5.211   0.821  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.461   5.263  -0.897  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.308   4.858  -0.532  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.833   2.429  -0.268  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.043   0.116   0.552  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.909  -1.800   0.068  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.650  -4.272  -0.340  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.462  -5.273  -0.611  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.441  -3.839  -0.486  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.173   1.062   1.626  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.625  -0.586   1.980  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.142  -0.078   1.914  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.503  -1.628   1.292  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.212  -0.107  -0.095  1.00  0.00           H  
HETATM   36  H15 UNL     1       3.427   1.695  -0.571  1.00  0.00           H  
HETATM   37  H16 UNL     1       4.061   0.757  -1.936  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.555   0.855  -1.930  1.00  0.00           H  
HETATM   39  H18 UNL     1       2.192  -0.851  -1.753  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    6
CONECT    3    4   25
CONECT    4    5    5   15
CONECT    5    6    7
CONECT    7    8   26
CONECT    8    9    9   13
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   21
CONECT   17   18   31   32
CONECT   18   19   33   34
CONECT   19   20   35
CONECT   20   21   36   37
CONECT   21   38   39
END

HMDB0060959
     RDKit          3D
4'-N-desmethylolanzapine
 39 42  0  0  0  0  0  0  0  0999 V2000
   -0.7461    4.7853   -0.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970    3.3327   -0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2619    2.2452   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211    1.0335   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1800    0.9769    0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    2.6211    0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0831   -0.1411    0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8240   -1.5314    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9580   -2.2764   -0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7990   -3.6361   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5503   -4.1948   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4339   -3.4264   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -2.0515   -0.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3044   -1.4272   -0.1066 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0265   -0.1903   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.0024   -0.0378 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    0.0300    1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460   -0.5427    1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -0.2541   -0.1393 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020    0.6781   -0.9820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284    0.1586   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8020    5.2112    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613    5.2631   -0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    4.8584   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    2.4288   -0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0427    0.1165    0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9091   -1.8003    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -4.2725   -0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616   -5.2730   -0.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -3.8386   -0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734    1.0616    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6248   -0.5856    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -0.0785    1.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.6279    1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118   -0.1066   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275    1.6945   -0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0607    0.7574   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5547    0.8550   -1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -0.8506   -1.7528 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
  5  7  1  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  6  2  1  0
 13  8  1  0
 21 16  1  0
 15  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Desmethylolanzapine	HMDB
N-Desmethylolanzapine	MeSH
Desmethylolanzapine	MeSH
N-Desmethyl-olanzapine	MeSH

Chemical Formula

C₁₆H₁₈N₄S

Average Molecular Weight

298.406

Monoisotopic Molecular Weight

298.125217286

IUPAC Name

5-methyl-8-(piperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaene

Traditional Name

5-methyl-8-(piperazin-1-yl)-4-thia-2,9-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),5,8,10,12-hexaene

CAS Registry Number

Not Available

SMILES

CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCNCC2)S1

InChI Identifier

InChI=1S/C16H18N4S/c1-11-10-12-15(20-8-6-17-7-9-20)18-13-4-2-3-5-14(13)19-16(12)21-11/h2-5,10,17,19H,6-9H2,1H3

InChI Key

FHPIXVHJEIZKJW-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
1,4-diazinane
Piperazine
2-aminothiophene
Imidolactam
Benzenoid
Heteroaromatic compound
Thiophene
Amidine
Azacycle
Secondary amine
Secondary aliphatic amine
Carboxylic acid amidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060959)
Liver (HMDB: HMDB0060959)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060959)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060959)

Cellular substructure

Cytoplasm (HMDB: HMDB0060959)
Membrane (HMDB: HMDB0060959)

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	0.064 g/L	ALOGPS
logP	2.64	ALOGPS
logP	3.01	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.17	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.66 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.58 m³·mol⁻¹	ChemAxon
Polarizability	33 Å³	ChemAxon
Number of Rings	4	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]+	166.96	31661259
DarkChem	[M-H]-	167.454	31661259
DeepCCS	[M+H]+	165.377	30932474
DeepCCS	[M-H]-	163.019	30932474
DeepCCS	[M-2H]-	196.136	30932474
DeepCCS	[M+Na]+	171.471	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	172.1	32859911
AllCCS	[M+Na-2H]-	171.6	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4'-N-desmethylolanzapine	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCNCC2)S1	4087.9	Standard polar	33892256
4'-N-desmethylolanzapine	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCNCC2)S1	2668.4	Standard non polar	33892256
4'-N-desmethylolanzapine	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCNCC2)S1	2893.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4'-N-desmethylolanzapine,1TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	2801.8	Semi standard non polar	33892256
4'-N-desmethylolanzapine,1TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	2694.3	Standard non polar	33892256
4'-N-desmethylolanzapine,1TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	4175.7	Standard polar	33892256
4'-N-desmethylolanzapine,1TMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C)CC2)S1	3015.4	Semi standard non polar	33892256
4'-N-desmethylolanzapine,1TMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C)CC2)S1	2923.8	Standard non polar	33892256
4'-N-desmethylolanzapine,1TMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C)CC2)S1	4585.5	Standard polar	33892256
4'-N-desmethylolanzapine,2TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C)CC1	2900.8	Semi standard non polar	33892256
4'-N-desmethylolanzapine,2TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C)CC1	2950.8	Standard non polar	33892256
4'-N-desmethylolanzapine,2TMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C)CC1	3987.8	Standard polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	2964.0	Semi standard non polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	2892.4	Standard non polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCNCC1	4218.7	Standard polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)S1	3239.5	Semi standard non polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)S1	3116.6	Standard non polar	33892256
4'-N-desmethylolanzapine,1TBDMS,isomer #2	CC1=CC2=C(NC3=CC=CC=C3N=C2N2CCN([Si](C)(C)C(C)(C)C)CC2)S1	4820.6	Standard polar	33892256
4'-N-desmethylolanzapine,2TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C(C)(C)C)CC1	3279.5	Semi standard non polar	33892256
4'-N-desmethylolanzapine,2TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C(C)(C)C)CC1	3340.5	Standard non polar	33892256
4'-N-desmethylolanzapine,2TBDMS,isomer #1	CC1=CC2=C(S1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C1N=C2N1CCN([Si](C)(C)C(C)(C)C)CC1	4113.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-N-desmethylolanzapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001c-9080000000-faa8849c72b6d869bd37	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-N-desmethylolanzapine 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 - 4'-N-desmethylolanzapine 10V, Positive-QTOF	splash10-0002-0090000000-e6173f65a5be854020d4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 20V, Positive-QTOF	splash10-0002-0090000000-c07ba5509b5f363be715	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 40V, Positive-QTOF	splash10-0002-9410000000-5677fd4bc90081f13b65	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 10V, Negative-QTOF	splash10-0002-0090000000-091ff8e9e22b3d41c509	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 20V, Negative-QTOF	splash10-0a4i-0090000000-dc8ea6f0e8d2788f620f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 40V, Negative-QTOF	splash10-0006-9340000000-f4df07581c100ebfad1a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 10V, Positive-QTOF	splash10-0002-0090000000-b3cb1faf775243f00caf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 20V, Positive-QTOF	splash10-0002-0090000000-b3cb1faf775243f00caf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 40V, Positive-QTOF	splash10-01ox-2190000000-c3e7182e256251f3c25b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 10V, Negative-QTOF	splash10-0002-0090000000-26a389783719b34ab6fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 20V, Negative-QTOF	splash10-0002-0090000000-26a389783719b34ab6fe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-N-desmethylolanzapine 40V, Negative-QTOF	splash10-03gl-2390000000-04ea41e24be59b5d9741	2021-09-24	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

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

135446209

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 4'-N-desmethylolanzapine (HMDB0060959)

MOL for HMDB0060959 (4'-N-desmethylolanzapine)

3D MOL for HMDB0060959 (4'-N-desmethylolanzapine)

3D SDF for HMDB0060959 (4'-N-desmethylolanzapine)

3D-SDF for HMDB0060959 (4'-N-desmethylolanzapine)

PDB for HMDB0060959 (4'-N-desmethylolanzapine)

3D PDB for HMDB0060959 (4'-N-desmethylolanzapine)

SMILES for HMDB0060959 (4'-N-desmethylolanzapine)

INCHI for HMDB0060959 (4'-N-desmethylolanzapine)

Structure for HMDB0060959 (4'-N-desmethylolanzapine)

3D Structure for HMDB0060959 (4'-N-desmethylolanzapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra