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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:24 UTC

Update Date

2019-07-23 07:15:07 UTC

HMDB ID

HMDB0060801

Secondary Accession Numbers

HMDB60801

Metabolite Identification

Common Name

8-Hydroxyamoxapine

Description

8-Hydroxyamoxapine 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 significant number of articles have been published on 8-Hydroxyamoxapine.

Structure

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

HMDB0060801
     RDKit          3D
8-Hydroxyamoxapine
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.1052   -2.9065   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -1.7615    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -0.5330    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299    0.6324    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408    0.5407    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.6792    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.8058    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -0.9734    0.3089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.1615    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126   -0.7371    0.2068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4086    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.6951    1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -1.4041   -0.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661   -2.4346   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725   -1.6402   -0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1365    1.2653   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    1.7344   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    3.0866   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    3.7144   -1.4742 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638    3.9638   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    3.4408   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    2.0975    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    1.7646    0.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0947   -2.8835   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188   -0.4916    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    1.5996    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909   -2.7602   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2990    0.6625    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.9943    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -1.3210    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.2295    1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.7723   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.8044    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -3.2335   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -2.3888   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.1164   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    1.0463   -0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    5.0253   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604    4.1030    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  2  1  0
 15 10  1  0
 22 16  1  0
 23  5  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
M  END

  Mrv0541 07041312002D          

 23 26  0  0  0  0            999 V2000
    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
    5.2900   -2.3419    0.0000 N   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
    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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  9  2  0  0  0  0
 12  2  1  0  0  0  0
 12 10  2  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  3  1  0  0  0  0
 15 13  2  0  0  0  0
 16  4  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 11  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 20 14  1  0  0  0  0
 20 17  2  0  0  0  0
 21  7  1  0  0  0  0
 21  8  1  0  0  0  0
 21 17  1  0  0  0  0
 22 12  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060801

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(OC3=C(C=C(Cl)C=C3)C(=N2)N2CCNCC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16ClN3O2/c18-11-1-3-15-13(9-11)17(21-7-5-19-6-8-21)20-14-10-12(22)2-4-16(14)23-15/h1-4,9-10,19,22H,5-8H2

> <INCHI_KEY>
QDWNOKXUZTYVGO-UHFFFAOYSA-N

> <FORMULA>
C17H16ClN3O2

> <MOLECULAR_WEIGHT>
329.781

> <EXACT_MASS>
329.093104478

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.64355106975039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-10-(piperazin-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>
2.67

> <JCHEM_LOGP>
2.359759719318789

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.366324683257073

> <JCHEM_PKA_STRONGEST_BASIC>
8.6783338551377

> <JCHEM_POLAR_SURFACE_AREA>
57.09

> <JCHEM_REFRACTIVITY>
91.7973

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-chloro-10-(piperazin-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

$$$$

HMDB0060801
     RDKit          3D
8-Hydroxyamoxapine
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.1052   -2.9065   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -1.7615    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -0.5330    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299    0.6324    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408    0.5407    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.6792    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.8058    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -0.9734    0.3089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.1615    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126   -0.7371    0.2068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4086    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.6951    1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -1.4041   -0.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661   -2.4346   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725   -1.6402   -0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1365    1.2653   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    1.7344   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    3.0866   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    3.7144   -1.4742 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638    3.9638   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    3.4408   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    2.0975    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    1.7646    0.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0947   -2.8835   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188   -0.4916    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    1.5996    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909   -2.7602   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2990    0.6625    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.9943    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -1.3210    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.2295    1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.7723   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.8044    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -3.2335   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -2.3888   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.1164   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    1.0463   -0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    5.0253   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604    4.1030    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  2  1  0
 15 10  1  0
 22 16  1  0
 23  5  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      11.088   3.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.112   3.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.617   3.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.584   3.544   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.742  -3.099   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.339  -4.257   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.074  -1.712   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.671  -2.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.302   0.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.898   0.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.431   1.589   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.770   1.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.830   0.995   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.370   0.995   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.488   2.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.713   2.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.870  -0.209   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      12.902   1.135   0.000  0.00  0.00          Cl+0
HETATM   19  N   UNK     0       9.875  -4.372   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       6.330  -0.209   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       8.538  -1.597   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       1.298   1.135   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.100   3.165   0.000  0.00  0.00           O+0
CONECT    1    3   11                                                       
CONECT    2    4   12                                                       
CONECT    3    1   15                                                       
CONECT    4    2   16                                                       
CONECT    5    7   19                                                       
CONECT    6    8   19                                                       
CONECT    7    5   21                                                       
CONECT    8    6   21                                                       
CONECT    9   11   13                                                       
CONECT   10   12   14                                                       
CONECT   11    1    9   18                                                  
CONECT   12    2   10   22                                                  
CONECT   13    9   15   17                                                  
CONECT   14   10   16   20                                                  
CONECT   15    3   13   23                                                  
CONECT   16    4   14   23                                                  
CONECT   17   13   20   21                                                  
CONECT   18   11                                                            
CONECT   19    5    6                                                       
CONECT   20   14   17                                                       
CONECT   21    7    8   17                                                  
CONECT   22   12                                                            
CONECT   23   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0060801
HETATM    1  O1  UNL     1       5.105  -2.906  -0.169  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.351  -1.761   0.046  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.943  -0.533   0.223  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.230   0.632   0.439  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.841   0.541   0.477  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.200  -0.679   0.304  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.974  -1.806   0.091  1.00  0.00           C  
HETATM    8  N1  UNL     1       0.805  -0.973   0.309  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.212  -0.162   0.156  1.00  0.00           C  
HETATM   10  N2  UNL     1      -1.513  -0.737   0.207  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.385  -0.409   1.289  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.832  -0.695   1.050  1.00  0.00           C  
HETATM   13  N3  UNL     1      -4.099  -1.404  -0.180  1.00  0.00           N  
HETATM   14  C10 UNL     1      -3.066  -2.435  -0.317  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.873  -1.640  -0.870  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.137   1.265  -0.061  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.330   1.734  -0.570  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.403   3.087  -0.827  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -2.905   3.714  -1.474  1.00  0.00          CL  
HETATM   20  C15 UNL     1      -0.364   3.964  -0.602  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.807   3.441  -0.092  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.943   2.098   0.186  1.00  0.00           C  
HETATM   23  O2  UNL     1       2.214   1.765   0.700  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.095  -2.884  -0.203  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.019  -0.492   0.188  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.697   1.600   0.578  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.491  -2.760  -0.045  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.299   0.663   1.617  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.090  -0.994   2.209  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.294  -1.321   1.869  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.451   0.229   1.022  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.070  -0.772  -1.009  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.828  -2.804   0.706  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.370  -3.234  -1.002  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.088  -2.389  -1.082  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.184  -1.116  -1.784  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.147   1.046  -0.746  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.436   5.025  -0.809  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.660   4.103   0.102  1.00  0.00           H  
CONECT    1    2   24
CONECT    2    3    3    7
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   23
CONECT    6    7    7    8
CONECT    7   27
CONECT    8    9    9
CONECT    9   10   16
CONECT   10   11   15
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   32
CONECT   14   15   33   34
CONECT   15   35   36
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   20   20
CONECT   20   21   38
CONECT   21   22   22   39
CONECT   22   23
END

HMDB0060801
     RDKit          3D
8-Hydroxyamoxapine
 39 42  0  0  0  0  0  0  0  0999 V2000
    5.1052   -2.9065   -0.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -1.7615    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -0.5330    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2299    0.6324    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408    0.5407    0.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -0.6792    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744   -1.8058    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -0.9734    0.3089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2116   -0.1615    0.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126   -0.7371    0.2068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -0.4086    1.2890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321   -0.6951    1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -1.4041   -0.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0661   -2.4346   -0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725   -1.6402   -0.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1365    1.2653   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    1.7344   -0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    3.0866   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    3.7144   -1.4742 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3638    3.9638   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067    3.4408   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9427    2.0975    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2137    1.7646    0.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0947   -2.8835   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0188   -0.4916    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6970    1.5996    0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4909   -2.7602   -0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2990    0.6625    1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900   -0.9943    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941   -1.3210    1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.2295    1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0702   -0.7723   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8281   -2.8044    0.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3703   -3.2335   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0880   -2.3888   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -1.1164   -1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465    1.0463   -0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    5.0253   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604    4.1030    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
  7  2  1  0
 15 10  1  0
 22 16  1  0
 23  5  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 20 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆ClN₃O₂

Average Molecular Weight

329.781

Monoisotopic Molecular Weight

329.093104478

IUPAC Name

13-chloro-10-(piperazin-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-(piperazin-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

61443-78-5

SMILES

OC1=CC2=C(OC3=C(C=C(Cl)C=C3)C(=N2)N2CCNCC2)C=C1

InChI Identifier

InChI=1S/C17H16ClN3O2/c18-11-1-3-15-13(9-11)17(21-7-5-19-6-8-21)20-14-10-12(22)2-4-16(14)23-15/h1-4,9-10,19,22H,5-8H2

InChI Key

QDWNOKXUZTYVGO-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
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Imidolactam
Benzenoid
Amidine
Carboxylic acid amidine
Secondary aliphatic amine
Oxacycle
Ether
Azacycle
Secondary amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Amine
Organopnictogen 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 (HMDB: HMDB0060801)

Organ

Kidney (HMDB: HMDB0060801)
Liver (HMDB: HMDB0060801)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060801)

Cellular substructure

Cytoplasm (HMDB: HMDB0060801)
Membrane (HMDB: HMDB0060801)

Source

Endogenous

Endogenous (HMDB: HMDB0060801)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.36	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.37	ChemAxon
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.8 m³·mol⁻¹	ChemAxon
Polarizability	33.64 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]+	180.366	30932474
DeepCCS	[M-H]-	178.008	30932474
DeepCCS	[M-2H]-	211.763	30932474
DeepCCS	[M+Na]+	186.99	30932474
AllCCS	[M+H]+	174.1	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	177.1	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	173.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyamoxapine	OC1=CC2=C(OC3=C(C=C(Cl)C=C3)C(=N2)N2CCNCC2)C=C1	4314.3	Standard polar	33892256
8-Hydroxyamoxapine	OC1=CC2=C(OC3=C(C=C(Cl)C=C3)C(=N2)N2CCNCC2)C=C1	2927.6	Standard non polar	33892256
8-Hydroxyamoxapine	OC1=CC2=C(OC3=C(C=C(Cl)C=C3)C(=N2)N2CCNCC2)C=C1	3071.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyamoxapine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCNCC3)=NC2=C1	2997.3	Semi standard non polar	33892256
8-Hydroxyamoxapine,1TMS,isomer #2	C[Si](C)(C)N1CCN(C2=NC3=CC(O)=CC=C3OC3=CC=C(Cl)C=C23)CC1	3114.4	Semi standard non polar	33892256
8-Hydroxyamoxapine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C)CC3)=NC2=C1	3072.1	Semi standard non polar	33892256
8-Hydroxyamoxapine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C)CC3)=NC2=C1	3010.0	Standard non polar	33892256
8-Hydroxyamoxapine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C)CC3)=NC2=C1	4286.6	Standard polar	33892256
8-Hydroxyamoxapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCNCC3)=NC2=C1	3174.9	Semi standard non polar	33892256
8-Hydroxyamoxapine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC(O)=CC=C3OC3=CC=C(Cl)C=C23)CC1	3364.7	Semi standard non polar	33892256
8-Hydroxyamoxapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C(C)(C)C)CC3)=NC2=C1	3470.6	Semi standard non polar	33892256
8-Hydroxyamoxapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C(C)(C)C)CC3)=NC2=C1	3417.0	Standard non polar	33892256
8-Hydroxyamoxapine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2OC3=CC=C(Cl)C=C3C(N3CCN([Si](C)(C)C(C)(C)C)CC3)=NC2=C1	4412.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyamoxapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9f-9182000000-b8b8e53cfb28088f2cfd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyamoxapine GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9107000000-22028c9ad311da80bb01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyamoxapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 10V, Positive-QTOF	splash10-001i-0009000000-5e07284fce8eb5819c25	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 20V, Positive-QTOF	splash10-001i-0029000000-25daabc66b1e281ec7ab	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 40V, Positive-QTOF	splash10-0cdr-6970000000-72155ae7835c0318d6ec	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 10V, Negative-QTOF	splash10-004i-0009000000-b5b8162a95df4f9068f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 20V, Negative-QTOF	splash10-004i-0039000000-5114673474a52e69ca5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 40V, Negative-QTOF	splash10-0006-9140000000-9d2aee81881a32ddfd54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 10V, Negative-QTOF	splash10-004i-0009000000-317a80daeb1f485525d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 20V, Negative-QTOF	splash10-004i-1019000000-03dbb1ddc44bd4b23e2f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 40V, Negative-QTOF	splash10-001i-2092000000-c2da73db1263ba71f06e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 10V, Positive-QTOF	splash10-001i-0009000000-2a0b3ee37f0986f8fe94	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 20V, Positive-QTOF	splash10-001i-0039000000-dfb26f6afe4e3d81cb24	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyamoxapine 40V, Positive-QTOF	splash10-000i-1391000000-8ef4a881ac95f66f665c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

39784

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Hydroxyamoxapine

METLIN ID

Not Available

PubChem Compound

43656

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 8-Hydroxyamoxapine (HMDB0060801)

MOL for HMDB0060801 (8-Hydroxyamoxapine)

3D MOL for HMDB0060801 (8-Hydroxyamoxapine)

3D SDF for HMDB0060801 (8-Hydroxyamoxapine)

3D-SDF for HMDB0060801 (8-Hydroxyamoxapine)

PDB for HMDB0060801 (8-Hydroxyamoxapine)

3D PDB for HMDB0060801 (8-Hydroxyamoxapine)

SMILES for HMDB0060801 (8-Hydroxyamoxapine)

INCHI for HMDB0060801 (8-Hydroxyamoxapine)

Structure for HMDB0060801 (8-Hydroxyamoxapine)

3D Structure for HMDB0060801 (8-Hydroxyamoxapine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra