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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 02:12:58 UTC

Update Date

2021-09-26 22:59:14 UTC

HMDB ID

HMDB0248768

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Azasetron

Description

N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboximidic acid belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. Based on a literature review very few articles have been published on N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Azasetron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Azasetron 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

HMDB0248768
     RDKit          3D
Azasetron
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.7475    0.2124   -0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3198    0.3283   -0.4239 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.9212   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    1.6531   -2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    0.6547   -1.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    0.5410   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -0.0479    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.5308    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0694   -0.4025    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.8728    2.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    0.1335    0.3938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335    0.2407    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105    1.5927   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135    1.4270   -0.5452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -0.9921   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.7949   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.1373   -2.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    0.8984   -1.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -1.1175    2.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2171    2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -1.9597    4.2005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.7510    1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5103   -0.1682    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445    0.5284   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0605   -0.8191   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613    0.8718    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -0.2868   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    1.4407   -2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5607   -1.6021    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    0.1042    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.3343    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072    1.9238   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4754    0.5874    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369    0.4427    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224   -1.4310   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409   -1.5966    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893   -1.7275   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8618    0.3285   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -0.9107   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.7014   -2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9092    0.4059   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715   -1.4937    3.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -0.8261    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  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
  8 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24  2  1  0
 24  7  1  0
 17 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 23 44  1  0
M  END

  Mrv1572004221604522D          

 24 27  0  0  0  0            999 V2000
    4.3830    5.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1953    4.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    3.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1953    4.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251    5.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    5.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    3.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    5.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396    6.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251    5.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6183    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540    5.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    3.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396    7.1791    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    5.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685    4.7041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    3.4666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    3.4666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    3.8791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396    3.8791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 19 13  1  4  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21  8  1  0  0  0  0
 22 15  2  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248768

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(=O)COC2=C(C=C(Cl)C=C12)C(O)=NC1CN2CCC1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C17H20ClN3O3/c1-20-14-7-11(18)6-12(16(14)24-9-15(20)22)17(23)19-13-8-21-4-2-10(13)3-5-21/h6-7,10,13H,2-5,8-9H2,1H3,(H,19,23)

> <INCHI_KEY>
WUKZPHOXUVCQOR-UHFFFAOYSA-N

> <FORMULA>
C17H20ClN3O3

> <MOLECULAR_WEIGHT>
349.82

> <EXACT_MASS>
349.1193192

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.002477716777314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboximidic acid

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
-0.18629629142322465

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.138485575909132

> <JCHEM_PKA_STRONGEST_BASIC>
8.551502716843217

> <JCHEM_POLAR_SURFACE_AREA>
65.37

> <JCHEM_REFRACTIVITY>
91.21289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azasetron

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248768
     RDKit          3D
Azasetron
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.7475    0.2124   -0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3198    0.3283   -0.4239 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.9212   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    1.6531   -2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    0.6547   -1.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    0.5410   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -0.0479    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.5308    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0694   -0.4025    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.8728    2.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    0.1335    0.3938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335    0.2407    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105    1.5927   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135    1.4270   -0.5452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -0.9921   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.7949   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.1373   -2.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    0.8984   -1.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -1.1175    2.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2171    2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -1.9597    4.2005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.7510    1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5103   -0.1682    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445    0.5284   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0605   -0.8191   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613    0.8718    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -0.2868   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    1.4407   -2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5607   -1.6021    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    0.1042    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.3343    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072    1.9238   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4754    0.5874    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369    0.4427    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224   -1.4310   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409   -1.5966    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893   -1.7275   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8618    0.3285   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -0.9107   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.7014   -2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9092    0.4059   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715   -1.4937    3.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -0.8261    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  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
  8 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24  2  1  0
 24  7  1  0
 17 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       8.182   9.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.822   8.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.231   8.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.822   7.241   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.231   7.498   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.847  11.091   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.514  11.091   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.154   7.241   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.514   6.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.488   9.551   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.181  11.861   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.847   9.551   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.154   8.781   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.514   9.551   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.848   7.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.181   8.781   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.513   8.781   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       4.181  13.401   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       0.180   9.551   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       6.848   8.781   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -2.488   6.471   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       8.182   6.471   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.513   7.241   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.181   7.241   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4   10                                                       
CONECT    3    5   10                                                       
CONECT    4    2   21                                                       
CONECT    5    3   21                                                       
CONECT    6   11   12                                                       
CONECT    7   11   14                                                       
CONECT    8   13   21                                                       
CONECT    9   15   24                                                       
CONECT   10    2    3   13                                                  
CONECT   11    6    7   18                                                  
CONECT   12    6   16   17                                                  
CONECT   13    8   10   19                                                  
CONECT   14    7   16   20                                                  
CONECT   15    9   20   22                                                  
CONECT   16   12   14   24                                                  
CONECT   17   12   19   23                                                  
CONECT   18   11                                                            
CONECT   19   13   17                                                       
CONECT   20    1   14   15                                                  
CONECT   21    4    5    8                                                  
CONECT   22   15                                                            
CONECT   23   17                                                            
CONECT   24    9   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0248768
HETATM    1  C1  UNL     1       5.748   0.212  -0.312  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.320   0.328  -0.424  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.723   0.921  -1.563  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.355   1.653  -2.352  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.287   0.655  -1.820  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.562   0.541  -0.612  1.00  0.00           O  
HETATM    7  C4  UNL     1       2.144  -0.048   0.519  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.364  -0.531   1.556  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.069  -0.403   1.422  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.885  -0.873   2.436  1.00  0.00           O  
HETATM   11  N2  UNL     1      -0.624   0.133   0.394  1.00  0.00           N  
HETATM   12  C7  UNL     1      -2.034   0.241   0.300  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.511   1.593  -0.188  1.00  0.00           C  
HETATM   14  N3  UNL     1      -3.914   1.427  -0.545  1.00  0.00           N  
HETATM   15  C9  UNL     1      -4.557   0.413   0.268  1.00  0.00           C  
HETATM   16  C10 UNL     1      -4.085  -0.992  -0.127  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.652  -0.795  -0.632  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.799  -0.137  -2.007  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.908   0.898  -1.917  1.00  0.00           C  
HETATM   20  C14 UNL     1       1.888  -1.117   2.688  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.260  -1.217   2.770  1.00  0.00           C  
HETATM   22 CL1  UNL     1       3.952  -1.960   4.201  1.00  0.00          CL  
HETATM   23  C16 UNL     1       4.088  -0.751   1.763  1.00  0.00           C  
HETATM   24  C17 UNL     1       3.510  -0.168   0.643  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.245   0.528  -1.252  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.061  -0.819  -0.041  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.161   0.872   0.496  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.244  -0.287  -2.418  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.815   1.441  -2.438  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.561  -1.602   2.166  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.480   0.104   1.314  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.475   2.334   0.640  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.907   1.924  -1.063  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.475   0.587   1.341  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.637   0.443   0.009  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.722  -1.431  -0.895  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.041  -1.597   0.812  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.089  -1.727  -0.670  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.862   0.328  -2.344  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.175  -0.911  -2.733  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.792   1.701  -2.664  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.909   0.406  -2.038  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.272  -1.494   3.497  1.00  0.00           H  
HETATM   44  H20 UNL     1       5.164  -0.826   1.821  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   24
CONECT    3    4    4    5
CONECT    5    6   28   29
CONECT    6    7
CONECT    7    8    8   24
CONECT    8    9   20
CONECT    9   10   11   11
CONECT   10   30
CONECT   11   12
CONECT   12   13   17   31
CONECT   13   14   32   33
CONECT   14   15   19
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18   38
CONECT   18   19   39   40
CONECT   19   41   42
CONECT   20   21   21   43
CONECT   21   22   23
CONECT   23   24   24   44
END

HMDB0248768
     RDKit          3D
Azasetron
 44 47  0  0  0  0  0  0  0  0999 V2000
    5.7475    0.2124   -0.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3198    0.3283   -0.4239 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.9212   -1.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    1.6531   -2.3519 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2872    0.6547   -1.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    0.5410   -0.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -0.0479    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3643   -0.5308    1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0694   -0.4025    1.4220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.8728    2.4362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6241    0.1335    0.3938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335    0.2407    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105    1.5927   -0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135    1.4270   -0.5452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    0.4134    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0851   -0.9921   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.7949   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -0.1373   -2.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    0.8984   -1.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881   -1.1175    2.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2171    2.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9525   -1.9597    4.2005 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -0.7510    1.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5103   -0.1682    0.6430 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445    0.5284   -1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0605   -0.8191   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1613    0.8718    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445   -0.2868   -2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    1.4407   -2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5607   -1.6021    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    0.1042    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4751    2.3343    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9072    1.9238   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4754    0.5874    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6369    0.4427    0.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7224   -1.4310   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409   -1.5966    0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0893   -1.7275   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8618    0.3285   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753   -0.9107   -2.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919    1.7014   -2.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9092    0.4059   -2.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715   -1.4937    3.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -0.8261    1.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  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
  8 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24  2  1  0
 24  7  1  0
 17 12  1  0
 19 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 23 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboximidate	Generator
Azasetron HCL	ChEMBL
Azasetron, (+-)-isomer	MeSH
N-(1-azabicyclo(2.2.2)Oct-3-yl)-6-chloro-4-methyl-3-oxo-3,4 -dihydro-2H-1,4-benzoxazine-8-carboxamide hydrochloride	MeSH

Chemical Formula

C₁₇H₂₀ClN₃O₃

Average Molecular Weight

349.82

Monoisotopic Molecular Weight

349.1193192

IUPAC Name

N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboximidic acid

Traditional Name

azasetron

CAS Registry Number

Not Available

SMILES

CN1C(=O)COC2=C(C=C(Cl)C=C12)C(O)=NC1CN2CCC1CC2

InChI Identifier

InChI=1S/C17H20ClN3O3/c1-20-14-7-11(18)6-12(16(14)24-9-15(20)22)17(23)19-13-8-21-4-2-10(13)3-5-21/h6-7,10,13H,2-5,8-9H2,1H3,(H,19,23)

InChI Key

WUKZPHOXUVCQOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Benzoxazinones

Direct Parent

Benzoxazinones

Alternative Parents

Substituents

Benzoxazinone
Benzomorpholine
Quinuclidine
Alkyl aryl ether
Oxazinane
Piperidine
Aryl chloride
Benzenoid
Aryl halide
Tertiary carboxylic acid amide
Tertiary amine
Secondary carboxylic acid amide
Lactam
Tertiary aliphatic amine
Carboxamide group
Amino acid or derivatives
Carboxylic acid derivative
Ether
Azacycle
Oxacycle
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
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)

Source

Exogenous

Exogenous (HMDB: HMDB0248768)

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	1.11	ALOGPS
logP	-0.19	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	8.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	36 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
DeepCCS	[M-2H]-	206.172	30932474
DeepCCS	[M+Na]+	181.399	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.7	32859911
AllCCS	[M+NH4]+	181.2	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	179.5	32859911
AllCCS	[M+Na-2H]-	179.4	32859911
AllCCS	[M+HCOO]-	179.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azasetron	CN1C(=O)COC2=C(C=C(Cl)C=C12)C(O)=NC1CN2CCC1CC2	3608.6	Standard polar	33892256
Azasetron	CN1C(=O)COC2=C(C=C(Cl)C=C12)C(O)=NC1CN2CCC1CC2	3007.0	Standard non polar	33892256
Azasetron	CN1C(=O)COC2=C(C=C(Cl)C=C12)C(O)=NC1CN2CCC1CC2	3037.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Azasetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-0c00-2967000000-8dc387004e333bc1f1aa	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azasetron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azasetron GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azasetron GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Azasetron 35V, Positive-QTOF	splash10-0udi-0229000000-530c6122237acb9c4d3c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 10V, Positive-QTOF	splash10-0udi-0509000000-69dbd8336141d170d34d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 20V, Positive-QTOF	splash10-03di-0912000000-ab8e17fa67d2b82684d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 40V, Positive-QTOF	splash10-03di-0910000000-e7d77a04cf617ba6e2fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 10V, Negative-QTOF	splash10-0002-0009000000-d45faf64589f2912ef2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 20V, Negative-QTOF	splash10-006t-9428000000-2f1891fc6488ceafa8ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 40V, Negative-QTOF	splash10-00dl-9100000000-98a0e4a6e025e71ce4d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 10V, Positive-QTOF	splash10-0udi-0009000000-f21e455874bf5a280c30	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 20V, Positive-QTOF	splash10-0udi-0419000000-bb4fae8a27554596d92c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 40V, Positive-QTOF	splash10-03di-0931000000-8669bc3ee99e54887678	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 10V, Negative-QTOF	splash10-0002-0009000000-81d8519b24ded80f3292	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 20V, Negative-QTOF	splash10-0002-1019000000-0cd892df9e77d803c47f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azasetron 40V, Negative-QTOF	splash10-000t-5439000000-0583b54af7437f1ffa10	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

2177

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 Azasetron (HMDB0248768)

MOL for HMDB0248768 (Azasetron)

3D MOL for HMDB0248768 (Azasetron)

3D SDF for HMDB0248768 (Azasetron)

3D-SDF for HMDB0248768 (Azasetron)

PDB for HMDB0248768 (Azasetron)

3D PDB for HMDB0248768 (Azasetron)

SMILES for HMDB0248768 (Azasetron)

INCHI for HMDB0248768 (Azasetron)

Structure for HMDB0248768 (Azasetron)

3D Structure for HMDB0248768 (Azasetron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra