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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:26:52 UTC

Update Date

2021-09-26 22:57:08 UTC

HMDB ID

HMDB0247441

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Hydroxyloxapine

Description

8-Hydroxyloxapine belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring. Based on a literature review a small amount of articles have been published on 8-Hydroxyloxapine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-hydroxyloxapine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Hydroxyloxapine 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

HMDB0247441
     RDKit          3D
8-Hydroxyloxapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5052    0.0665   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096   -0.6005    0.1355 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.2523    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293    0.1785    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077   -0.4749    0.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.2173    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -1.1431    0.5383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -1.1090    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -2.3754    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480   -2.5472    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -3.8244    0.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1608   -1.4468    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6252   -0.1695    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.0072    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    1.3462    0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    1.8456   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    3.1438   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    3.7931   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    3.1379   -1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9032    3.9250   -1.8559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5649    1.8307   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    1.1539   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.3478   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -1.7577   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.2792   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3591   -0.5487   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548    1.0205   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351    0.0529    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    1.3303    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    1.1799    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -0.4203    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -3.2773    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -4.3557   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -1.5813    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591    0.7149    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7822    3.6625   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    4.8104   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    1.3216   -0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.8802   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -2.2834   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444   -2.3078   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647   -2.3704    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  1  0
 24  2  1  0
 22  6  1  0
 14  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 23 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END


  Mrv1572004251603072D          

 24 27  0  0  0  0            999 V2000
    5.6480   -3.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    1.6553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1517    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    1.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7548   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4673   -2.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3968   -0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1094   -1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0884    0.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1237    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837    0.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    1.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -0.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120    0.6078    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -0.1120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2900   -2.3419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.8553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6953    0.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8037    1.6953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  4  1  0  0  0  0
 16 14  2  0  0  0  0
 17  5  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  2  0  0  0  0
 21  1  1  0  0  0  0
 21  6  1  0  0  0  0
 21  7  1  0  0  0  0
 22  8  1  0  0  0  0
 22  9  1  0  0  0  0
 22 18  1  0  0  0  0
 23 13  1  0  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247441

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC1)C1=NC2=C(OC3=C1C=C(Cl)C=C3)C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18ClN3O2/c1-21-6-8-22(9-7-21)18-14-10-12(19)2-4-16(14)24-17-5-3-13(23)11-15(17)20-18/h2-5,10-11,23H,6-9H2,1H3

> <INCHI_KEY>
VNJRIWXLPIYFGI-UHFFFAOYSA-N

> <FORMULA>
C18H18ClN3O2

> <MOLECULAR_WEIGHT>
343.81

> <EXACT_MASS>
343.1087545

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.73742034583891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-6-ol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.1570371103333335

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.222534680012355

> <JCHEM_PKA_STRONGEST_BASIC>
7.161312677245811

> <JCHEM_POLAR_SURFACE_AREA>
48.3

> <JCHEM_REFRACTIVITY>
97.092

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-6-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247441
     RDKit          3D
8-Hydroxyloxapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5052    0.0665   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096   -0.6005    0.1355 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.2523    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293    0.1785    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077   -0.4749    0.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.2173    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -1.1431    0.5383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -1.1090    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -2.3754    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480   -2.5472    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -3.8244    0.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1608   -1.4468    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6252   -0.1695    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.0072    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    1.3462    0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    1.8456   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    3.1438   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    3.7931   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    3.1379   -1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9032    3.9250   -1.8559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5649    1.8307   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    1.1539   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.3478   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -1.7577   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.2792   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3591   -0.5487   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548    1.0205   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351    0.0529    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    1.3303    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    1.1799    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -0.4203    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -3.2773    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -4.3557   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -1.5813    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591    0.7149    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7822    3.6625   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    4.8104   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    1.3216   -0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.8802   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -2.2834   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444   -2.3078   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647   -2.3704    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  1  0
 24  2  1  0
 22  6  1  0
 14  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 23 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0      10.543  -5.759   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.088   3.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.112   3.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.617   3.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.584   3.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.742  -3.099   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.339  -4.256   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.074  -1.712   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.671  -2.869   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.302   0.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.898   0.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.431   1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.770   1.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.830   0.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.370   0.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.488   2.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.713   2.496   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.870  -0.209   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      12.902   1.135   0.000  0.00  0.00          Cl+0
HETATM   20  N   UNK     0       6.330  -0.209   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       9.875  -4.372   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       8.538  -1.597   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       1.298   1.135   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.100   3.165   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    4   12                                                       
CONECT    3    5   13                                                       
CONECT    4    2   16                                                       
CONECT    5    3   17                                                       
CONECT    6    8   21                                                       
CONECT    7    9   21                                                       
CONECT    8    6   22                                                       
CONECT    9    7   22                                                       
CONECT   10   12   14                                                       
CONECT   11   13   15                                                       
CONECT   12    2   10   19                                                  
CONECT   13    3   11   23                                                  
CONECT   14   10   16   18                                                  
CONECT   15   11   17   20                                                  
CONECT   16    4   14   24                                                  
CONECT   17    5   15   24                                                  
CONECT   18   14   20   22                                                  
CONECT   19   12                                                            
CONECT   20   15   18                                                       
CONECT   21    1    6    7                                                  
CONECT   22    8    9   18                                                  
CONECT   23   13                                                            
CONECT   24   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0247441
HETATM    1  C1  UNL     1       4.505   0.066  -0.976  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.910  -0.601   0.135  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.404   0.252   1.144  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.929   0.179   1.377  1.00  0.00           C  
HETATM    5  N2  UNL     1       1.208  -0.475   0.309  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.188  -0.217   0.244  1.00  0.00           C  
HETATM    7  N3  UNL     1      -1.021  -1.143   0.538  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.442  -1.109   0.543  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.975  -2.375   0.614  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.348  -2.547   0.629  1.00  0.00           C  
HETATM   11  O1  UNL     1      -4.909  -3.824   0.701  1.00  0.00           O  
HETATM   12  C8  UNL     1      -5.161  -1.447   0.573  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.625  -0.169   0.501  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.270  -0.007   0.486  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.884   1.346   0.411  1.00  0.00           O  
HETATM   16  C11 UNL     1      -1.710   1.846  -0.096  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.826   3.144  -0.542  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.721   3.793  -1.085  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.484   3.138  -1.175  1.00  0.00           C  
HETATM   20 CL1  UNL     1       1.903   3.925  -1.856  1.00  0.00          CL  
HETATM   21  C15 UNL     1       0.565   1.831  -0.717  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.497   1.154  -0.175  1.00  0.00           C  
HETATM   23  C17 UNL     1       1.779  -1.348  -0.674  1.00  0.00           C  
HETATM   24  C18 UNL     1       3.152  -1.758  -0.168  1.00  0.00           C  
HETATM   25  H1  UNL     1       3.833   0.279  -1.814  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.359  -0.549  -1.380  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.955   1.021  -0.587  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.935   0.053   2.098  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.639   1.330   0.905  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.476   1.180   1.601  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.742  -0.420   2.315  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.376  -3.277   0.660  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.126  -4.356  -0.151  1.00  0.00           H  
HETATM   34  H10 UNL     1      -6.231  -1.581   0.585  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.259   0.715   0.456  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.782   3.662  -0.469  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.786   4.810  -1.441  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.525   1.322  -0.794  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.913  -0.880  -1.667  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.213  -2.283  -0.834  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.644  -2.308  -0.986  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.065  -2.370   0.763  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   24
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   23
CONECT    6    7    7   22
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   32
CONECT   10   11   12   12
CONECT   11   33
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   21
CONECT   21   22   22   38
CONECT   23   24   39   40
CONECT   24   41   42
END

HMDB0247441
     RDKit          3D
8-Hydroxyloxapine
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.5052    0.0665   -0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9096   -0.6005    0.1355 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    0.2523    1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9293    0.1785    1.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077   -0.4749    0.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1883   -0.2173    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -1.1431    0.5383 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4424   -1.1090    0.5425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9750   -2.3754    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3480   -2.5472    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -3.8244    0.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1608   -1.4468    0.5726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6252   -0.1695    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2695   -0.0072    0.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8844    1.3462    0.4110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7098    1.8456   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    3.1438   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    3.7931   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4838    3.1379   -1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9032    3.9250   -1.8559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5649    1.8307   -0.7168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4971    1.1539   -0.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.3478   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -1.7577   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.2792   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3591   -0.5487   -1.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548    1.0205   -0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351    0.0529    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    1.3303    0.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765    1.1799    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415   -0.4203    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -3.2773    0.6600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1256   -4.3557   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313   -1.5813    0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591    0.7149    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7822    3.6625   -0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    4.8104   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250    1.3216   -0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132   -0.8802   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -2.2834   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444   -2.3078   -0.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0647   -2.3704    0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  5 23  1  0
 23 24  1  0
 24  2  1  0
 22  6  1  0
 14  8  1  0
 22 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 21 38  1  0
 23 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroxyloxapine	MeSH

Chemical Formula

C₁₈H₁₈ClN₃O₂

Average Molecular Weight

343.81

Monoisotopic Molecular Weight

343.1087545

IUPAC Name

13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-6-ol

Traditional Name

13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-6-ol

CAS Registry Number

Not Available

SMILES

CN1CCN(CC1)C1=NC2=C(OC3=C1C=C(Cl)C=C3)C=CC(O)=C2

InChI Identifier

InChI=1S/C18H18ClN3O2/c1-21-6-8-22(9-7-21)18-14-10-12(19)2-4-16(14)24-17-5-3-13(23)11-15(17)20-18/h2-5,10-11,23H,6-9H2,1H3

InChI Key

VNJRIWXLPIYFGI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazepines

Sub Class

Dibenzoxazepines

Direct Parent

Dibenzoxazepines

Alternative Parents

Substituents

Dibenzoxazepine
Diaryl ether
1-hydroxy-2-unsubstituted benzenoid
N-methylpiperazine
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Imidolactam
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Amidine
Amine
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
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 (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	2.69	ALOGPS
logP	3.16	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	7.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	97.09 m³·mol⁻¹	ChemAxon
Polarizability	35.74 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+H]+	180.881	30932474
DeepCCS	[M-H]-	178.523	30932474
DeepCCS	[M-2H]-	212.032	30932474
DeepCCS	[M+Na]+	187.259	30932474
AllCCS	[M+H]+	178.4	32859911
AllCCS	[M+H-H2O]+	175.4	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	181.9	32859911
AllCCS	[M-H]-	177.2	32859911
AllCCS	[M+Na-2H]-	176.5	32859911
AllCCS	[M+HCOO]-	175.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.1471 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	838.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	342.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	343.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	568.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	738.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	195.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	805.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	379.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	87.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyloxapine	CN1CCN(CC1)C1=NC2=C(OC3=C1C=C(Cl)C=C3)C=CC(O)=C2	4134.8	Standard polar	33892256
8-Hydroxyloxapine	CN1CCN(CC1)C1=NC2=C(OC3=C1C=C(Cl)C=C3)C=CC(O)=C2	2897.2	Standard non polar	33892256
8-Hydroxyloxapine	CN1CCN(CC1)C1=NC2=C(OC3=C1C=C(Cl)C=C3)C=CC(O)=C2	2993.7	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 - 8-Hydroxyloxapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4m-9066000000-bfff1bf2a7a5aad59f5a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyloxapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyloxapine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyloxapine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 10V, Positive-QTOF	splash10-0006-0009000000-e5c6aadc02842ff8e002	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 20V, Positive-QTOF	splash10-0006-0019000000-99c5d0ffc724b20d4596	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 40V, Positive-QTOF	splash10-05g0-8691000000-502917ce0cf135b2dd69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 10V, Negative-QTOF	splash10-0006-0009000000-f0bd17c95b260e402da2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 20V, Negative-QTOF	splash10-0006-0019000000-112677e9a59e3dbf3a28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 40V, Negative-QTOF	splash10-006x-5494000000-c2bc83cf13710b551a3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 10V, Positive-QTOF	splash10-0006-0009000000-9abc48cbb0c968451a26	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 20V, Positive-QTOF	splash10-0006-0019000000-157208e00dfa972d3150	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 40V, Positive-QTOF	splash10-000i-0291000000-dfe7714f847a0db37d25	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 10V, Negative-QTOF	splash10-0006-0009000000-cacab0cef345b2ab6041	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 20V, Negative-QTOF	splash10-0006-1039000000-0660cfa7f6bc260dac4e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyloxapine 40V, Negative-QTOF	splash10-008i-2093000000-bac0a97c6cca0621dbbe	2021-10-12	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

39783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

43655

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 8-Hydroxyloxapine (HMDB0247441)

MOL for HMDB0247441 (8-Hydroxyloxapine)

3D MOL for HMDB0247441 (8-Hydroxyloxapine)

3D SDF for HMDB0247441 (8-Hydroxyloxapine)

3D-SDF for HMDB0247441 (8-Hydroxyloxapine)

PDB for HMDB0247441 (8-Hydroxyloxapine)

3D PDB for HMDB0247441 (8-Hydroxyloxapine)

SMILES for HMDB0247441 (8-Hydroxyloxapine)

INCHI for HMDB0247441 (8-Hydroxyloxapine)

Structure for HMDB0247441 (8-Hydroxyloxapine)

3D Structure for HMDB0247441 (8-Hydroxyloxapine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra