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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:00:15 UTC

Update Date

2021-09-26 23:16:58 UTC

HMDB ID

HMDB0259433

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zolmitriptan N-Oxide

Description

2-{5-[(2-hydroxy-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-indol-3-yl}-N,N-dimethylethanamine oxide belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review very few articles have been published on 2-{5-[(2-hydroxy-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-indol-3-yl}-N,N-dimethylethanamine oxide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zolmitriptan n-oxide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zolmitriptan N-Oxide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259433
     RDKit          3D
Zolmitriptan N-Oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.4120   -0.8446   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    0.5153    0.2719 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7204    0.5738    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    1.2330   -0.8189 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.5055    1.1582    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    1.8663   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298    0.9029   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    0.6660   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -0.3146   -2.9025 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.7270   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531   -1.6890   -1.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -1.8953   -0.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -1.1403    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850   -1.3299    1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071   -0.4376    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438   -0.6635    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3448    0.5873    0.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    1.5516    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3579    2.7384    0.1637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508    0.9603    1.3954 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.1925    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    0.0181   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -1.4965    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886   -0.9637   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509   -1.2745    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.5751    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053    1.4980    1.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6342   -0.2888    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.8533    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008    0.3696    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962    2.3576    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    2.6965   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203    1.1968   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -0.7051   -3.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.2787   -2.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936   -2.6641   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -1.0850    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -2.3702    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -0.6173    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258   -0.7702   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3928   -1.4649    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.4768    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4863    0.4185    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  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
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 18 20  1  0
 13 21  1  0
 21 22  2  0
 22  7  1  0
 22 10  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END


  Mrv1652309122100002D          

 22 24  0  0  0  0            999 V2000
   -1.7153    2.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.2450    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3720    2.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970    2.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819    2.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520    1.4370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6757    1.9652    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  9 10  2  0  0  0  0
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 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
  2 22  1  0  0  0  0
M  CHG  2   2   1  22  -1
M  END
> <DATABASE_ID>
HMDB0259433

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)([O-])CCC1=CNC2=C1C=C(CC1COC(=O)N1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H21N3O3/c1-19(2,21)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-22-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)

> <INCHI_KEY>
GZYCQRZFJIZOKU-UHFFFAOYSA-N

> <FORMULA>
C16H21N3O3

> <MOLECULAR_WEIGHT>
303.362

> <EXACT_MASS>
303.158291548

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.45312472293141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N-dimethyl-2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethanamine oxide

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
0.9185001043333347

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.682502483900734

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.683176302077953

> <JCHEM_PKA_STRONGEST_BASIC>
4.422077153247667

> <JCHEM_POLAR_SURFACE_AREA>
77.18

> <JCHEM_REFRACTIVITY>
84.48409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N,N-dimethyl-2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethanamine oxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259433
     RDKit          3D
Zolmitriptan N-Oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.4120   -0.8446   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    0.5153    0.2719 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7204    0.5738    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    1.2330   -0.8189 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.5055    1.1582    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    1.8663   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298    0.9029   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    0.6660   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -0.3146   -2.9025 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.7270   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531   -1.6890   -1.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -1.8953   -0.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -1.1403    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850   -1.3299    1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071   -0.4376    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438   -0.6635    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3448    0.5873    0.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    1.5516    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3579    2.7384    0.1637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508    0.9603    1.3954 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.1925    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    0.0181   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -1.4965    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886   -0.9637   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509   -1.2745    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.5751    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053    1.4980    1.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6342   -0.2888    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.8533    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008    0.3696    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962    2.3576    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    2.6965   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203    1.1968   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -0.7051   -3.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.2787   -2.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936   -2.6641   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -1.0850    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -2.3702    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -0.6173    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258   -0.7702   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3928   -1.4649    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.4768    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4863    0.4185    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  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  2  0
 18 20  1  0
 13 21  1  0
 21 22  2  0
 22  7  1  0
 22 10  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0      -3.202   4.657   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.726   3.192   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      -4.191   2.717   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.952   2.682   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.428   4.147   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.968   4.147   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.873   5.393   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       6.444   2.682   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -1.261   3.668   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   16                                                       
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0259433
HETATM    1  C1  UNL     1      -3.412  -0.845  -0.121  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.628   0.515   0.272  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -4.720   0.574   1.243  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.056   1.233  -0.819  1.00  0.00           O1-
HETATM    5  C3  UNL     1      -2.505   1.158   0.884  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.647   1.866  -0.140  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.130   0.903  -1.128  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.513   0.666  -2.420  1.00  0.00           C  
HETATM    9  N2  UNL     1      -0.729  -0.315  -2.902  1.00  0.00           N  
HETATM   10  C7  UNL     1       0.149  -0.727  -1.981  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.153  -1.689  -1.976  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.924  -1.895  -0.840  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.686  -1.140   0.281  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.485  -1.330   1.491  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.707  -0.438   1.527  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.644  -0.663   0.387  1.00  0.00           C  
HETATM   17  O2  UNL     1       5.345   0.587   0.317  1.00  0.00           O  
HETATM   18  C14 UNL     1       4.353   1.552   0.581  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.358   2.738   0.164  1.00  0.00           O  
HETATM   20  N3  UNL     1       3.351   0.960   1.395  1.00  0.00           N  
HETATM   21  C15 UNL     1       0.693  -0.193   0.269  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.080   0.018  -0.862  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.199  -1.497   0.351  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.589  -0.964  -1.229  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.451  -1.275   0.179  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.668   0.575   0.663  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.605   1.498   1.821  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.634  -0.289   1.925  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.817   1.853   1.702  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.901   0.370   1.405  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.796   2.358   0.398  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.201   2.696  -0.622  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.320   1.197  -2.944  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.791  -0.705  -3.861  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.334  -2.279  -2.862  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.694  -2.664  -0.900  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.907  -1.085   2.430  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.841  -2.370   1.632  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.225  -0.617   2.488  1.00  0.00           H  
HETATM   40  H18 UNL     1       4.126  -0.770  -0.586  1.00  0.00           H  
HETATM   41  H19 UNL     1       5.393  -1.465   0.566  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.540   1.477   1.793  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.486   0.418   1.149  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    8   22
CONECT    8    9   33
CONECT    9   10   34
CONECT   10   11   11   22
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   21
CONECT   14   15   37   38
CONECT   15   16   20   39
CONECT   16   17   40   41
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   42
CONECT   21   22   22   43
END

HMDB0259433
     RDKit          3D
Zolmitriptan N-Oxide
 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.4120   -0.8446   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282    0.5153    0.2719 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.7204    0.5738    1.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0558    1.2330   -0.8189 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.5055    1.1582    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466    1.8663   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298    0.9029   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5134    0.6660   -2.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -0.3146   -2.9025 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1490   -0.7270   -1.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1531   -1.6890   -1.9764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9241   -1.8953   -0.8397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -1.1403    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850   -1.3299    1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7071   -0.4376    1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438   -0.6635    0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3448    0.5873    0.3167 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    1.5516    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3579    2.7384    0.1637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508    0.9603    1.3954 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.1925    0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802    0.0181   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -1.4965    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5886   -0.9637   -1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509   -1.2745    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.5751    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6053    1.4980    1.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6342   -0.2888    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169    1.8533    1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008    0.3696    1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7962    2.3576    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2008    2.6965   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203    1.1968   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -0.7051   -3.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -2.2787   -2.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936   -2.6641   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9066   -1.0850    2.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -2.3702    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255   -0.6173    2.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258   -0.7702   -0.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3928   -1.4649    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401    1.4768    1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4863    0.4185    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  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  2  0
 18 20  1  0
 13 21  1  0
 21 22  2  0
 22  7  1  0
 22 10  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 20 42  1  0
 21 43  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₁N₃O₃

Average Molecular Weight

303.362

Monoisotopic Molecular Weight

303.158291548

IUPAC Name

N,N-dimethyl-2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethanamine oxide

Traditional Name

N,N-dimethyl-2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethanamine oxide

CAS Registry Number

Not Available

SMILES

C[N+](C)([O-])CCC1=CNC2=C1C=C(CC1COC(=O)N1)C=C2

InChI Identifier

InChI=1S/C16H21N3O3/c1-19(2,21)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-22-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)

InChI Key

GZYCQRZFJIZOKU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Oxazolidinone
Substituted pyrrole
Benzenoid
Oxazolidine
Pyrrole
Carbamic acid ester
Trialkyl amine oxide
Heteroaromatic compound
Trisubstituted n-oxide
N-oxide
Azacycle
Oxacycle
Organonitrogen compound
Organic zwitterion
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic salt
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	-0.16	ALOGPS
logP	0.92	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	4.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.18 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	84.48 m³·mol⁻¹	ChemAxon
Polarizability	32.45 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
DeepCCS	[M+H]+	155.026	30932474
DeepCCS	[M-H]-	152.664	30932474
DeepCCS	[M-2H]-	186.33	30932474
DeepCCS	[M+Na]+	161.524	30932474
AllCCS	[M+H]+	172.9	32859911
AllCCS	[M+H-H2O]+	169.6	32859911
AllCCS	[M+NH4]+	176.0	32859911
AllCCS	[M+Na]+	176.8	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zolmitriptan N-Oxide	C[N+](C)([O-])CCC1=CNC2=C1C=C(CC1COC(=O)N1)C=C2	3967.4	Standard polar	33892256
Zolmitriptan N-Oxide	C[N+](C)([O-])CCC1=CNC2=C1C=C(CC1COC(=O)N1)C=C2	2365.0	Standard non polar	33892256
Zolmitriptan N-Oxide	C[N+](C)([O-])CCC1=CNC2=C1C=C(CC1COC(=O)N1)C=C2	3082.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zolmitriptan N-Oxide,1TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3)C=C12	2829.2	Semi standard non polar	33892256
Zolmitriptan N-Oxide,1TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3)C=C12	2779.9	Standard non polar	33892256
Zolmitriptan N-Oxide,1TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3)C=C12	3972.6	Standard polar	33892256
Zolmitriptan N-Oxide,1TMS,isomer #2	C[N+](C)([O-])CCC1=C[NH]C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	2797.5	Semi standard non polar	33892256
Zolmitriptan N-Oxide,1TMS,isomer #2	C[N+](C)([O-])CCC1=C[NH]C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	2750.8	Standard non polar	33892256
Zolmitriptan N-Oxide,1TMS,isomer #2	C[N+](C)([O-])CCC1=C[NH]C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	3571.6	Standard polar	33892256
Zolmitriptan N-Oxide,2TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	2764.4	Semi standard non polar	33892256
Zolmitriptan N-Oxide,2TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	2772.3	Standard non polar	33892256
Zolmitriptan N-Oxide,2TMS,isomer #1	C[N+](C)([O-])CCC1=CN([Si](C)(C)C)C2=CC=C(CC3COC(=O)N3[Si](C)(C)C)C=C12	3280.8	Standard polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC[N+](C)(C)[O-])C2=CC(CC3COC(=O)N3)=CC=C21	3039.7	Semi standard non polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC[N+](C)(C)[O-])C2=CC(CC3COC(=O)N3)=CC=C21	3000.7	Standard non polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C=C(CC[N+](C)(C)[O-])C2=CC(CC3COC(=O)N3)=CC=C21	3936.4	Standard polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2[NH]C=C(CC[N+](C)(C)[O-])C2=C1	3046.7	Semi standard non polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2[NH]C=C(CC[N+](C)(C)[O-])C2=C1	2988.0	Standard non polar	33892256
Zolmitriptan N-Oxide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2[NH]C=C(CC[N+](C)(C)[O-])C2=C1	3565.7	Standard polar	33892256
Zolmitriptan N-Oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2C(=C1)C(CC[N+](C)(C)[O-])=CN2[Si](C)(C)C(C)(C)C	3199.9	Semi standard non polar	33892256
Zolmitriptan N-Oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2C(=C1)C(CC[N+](C)(C)[O-])=CN2[Si](C)(C)C(C)(C)C	3204.2	Standard non polar	33892256
Zolmitriptan N-Oxide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)OCC1CC1=CC=C2C(=C1)C(CC[N+](C)(C)[O-])=CN2[Si](C)(C)C(C)(C)C	3312.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zolmitriptan N-Oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6290000000-68a34b3d5a73d8d92321	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zolmitriptan N-Oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

8510598

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Zolmitriptan N-Oxide (HMDB0259433)

MOL for HMDB0259433 (Zolmitriptan N-Oxide)

3D MOL for HMDB0259433 (Zolmitriptan N-Oxide)

3D SDF for HMDB0259433 (Zolmitriptan N-Oxide)

3D-SDF for HMDB0259433 (Zolmitriptan N-Oxide)

PDB for HMDB0259433 (Zolmitriptan N-Oxide)

3D PDB for HMDB0259433 (Zolmitriptan N-Oxide)

SMILES for HMDB0259433 (Zolmitriptan N-Oxide)

INCHI for HMDB0259433 (Zolmitriptan N-Oxide)

Structure for HMDB0259433 (Zolmitriptan N-Oxide)

3D Structure for HMDB0259433 (Zolmitriptan N-Oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra