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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:45:23 UTC

Update Date

2021-09-26 23:05:32 UTC

HMDB ID

HMDB0252740

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glaziovine

Description

11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. 11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaen-4-one is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Glaziovine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Glaziovine 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

HMDB0252740
     RDKit          3D
Glaziovine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.9684    0.5419    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845    1.3090    0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    0.6365    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.7605    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.3722    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -0.5900    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821    0.7746   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105    1.3944    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    2.7916   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    1.2314   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.3703   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    3.5175   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4249    3.6805    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    4.7911    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4145    2.5662    1.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670    1.4344    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102   -0.0115   -0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -1.0923   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457   -2.3466   -0.7640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -2.8994   -0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -3.2787   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -2.8365    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -0.2282    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293    1.2247    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    0.0068   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.3359    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    3.2355    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    2.2754   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280    4.3713   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    2.7155    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    0.6083    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0095   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.0858   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.2140    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -2.3853   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065   -2.7268    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -4.0039   -0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -3.6753    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -4.1804   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765   -3.2983   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -3.1647    1.2131 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  8  3  1  0
 16 10  1  0
 22  5  1  0
 18  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END


  Mrv1533004241518122D          

 22 25  0  0  0  0            999 V2000
    2.1761   -3.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938   -3.1326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290   -2.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8465   -2.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -0.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774    0.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    0.5359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    1.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3063    0.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930    0.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -0.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9908    0.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8158    0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0473   -0.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8039   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -1.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0819   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467   -1.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -2.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2994   -0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
  5 22  2  0  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252740

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C3C(CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3

> <INCHI_KEY>
PNJUPRNTSWJWAX-UHFFFAOYSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.354

> <EXACT_MASS>
297.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.249984138005914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.3109943059999996

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.839293201220187

> <JCHEM_PKA_STRONGEST_BASIC>
7.2590150109691365

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
87.78769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252740
     RDKit          3D
Glaziovine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.9684    0.5419    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845    1.3090    0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    0.6365    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.7605    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.3722    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -0.5900    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821    0.7746   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105    1.3944    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    2.7916   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    1.2314   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.3703   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    3.5175   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4249    3.6805    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    4.7911    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4145    2.5662    1.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670    1.4344    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102   -0.0115   -0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -1.0923   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457   -2.3466   -0.7640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -2.8994   -0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -3.2787   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -2.8365    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -0.2282    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293    1.2247    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    0.0068   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.3359    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    3.2355    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    2.2754   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280    4.3713   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    2.7155    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    0.6083    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0095   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.0858   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.2140    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -2.3853   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065   -2.7268    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -4.0039   -0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -3.6753    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -4.1804   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765   -3.2983   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -3.1647    1.2131 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  8  3  1  0
 16 10  1  0
 22  5  1  0
 18  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.062  -6.868   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.215  -5.847   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.907  -4.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.447  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.139  -2.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.625  -1.298   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.638   0.242   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.978   1.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.991   2.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.305   0.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.774   0.683   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.449   0.757   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.989   0.744   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -0.596   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.288  -0.609   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.967  -1.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.427  -1.910   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.753  -1.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.060  -3.318   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.521  -3.806   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.292  -1.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19   12   20   22                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22   19    5   10                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0252740
HETATM    1  C1  UNL     1       4.968   0.542   0.318  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.784   1.309   0.201  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.578   0.637   0.142  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.499  -0.760   0.194  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.289  -1.372   0.132  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.179  -0.590   0.020  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.182   0.775  -0.036  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.410   1.394   0.026  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.464   2.792  -0.028  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.247   1.231  -0.169  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.275   2.370  -1.073  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.819   3.517  -0.748  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.425   3.680   0.563  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.952   4.791   0.878  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.414   2.566   1.490  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.867   1.434   1.144  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.910  -0.011  -0.797  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.200  -1.092  -0.046  1.00  0.00           C  
HETATM   19  N1  UNL     1      -1.146  -2.347  -0.764  1.00  0.00           N  
HETATM   20  C16 UNL     1      -2.494  -2.899  -0.743  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.283  -3.279  -0.125  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.092  -2.836   0.177  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.883  -0.228   1.123  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.829   1.225   0.509  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.084   0.007  -0.664  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.391  -1.336   0.282  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.379   3.236   0.020  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.837   2.275  -2.042  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.828   4.371  -1.456  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.880   2.716   2.479  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.862   0.608   1.838  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.990   0.010  -0.592  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.652  -0.086  -1.868  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.570  -1.214   0.990  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.154  -2.385  -1.456  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.907  -2.727   0.268  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.477  -4.004  -0.890  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.829  -3.675   0.777  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.209  -4.180  -0.803  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.877  -3.298  -0.481  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.341  -3.165   1.213  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   22
CONECT    6    7   18
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   27
CONECT   10   11   16   17
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14   14   15
CONECT   15   16   16   30
CONECT   16   31
CONECT   17   18   32   33
CONECT   18   19   34
CONECT   19   20   21
CONECT   20   35   36   37
CONECT   21   22   38   39
CONECT   22   40   41
END

HMDB0252740
     RDKit          3D
Glaziovine
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.9684    0.5419    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7845    1.3090    0.2006 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    0.6365    0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.7605    0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.3722    0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1788   -0.5900    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821    0.7746   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105    1.3944    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    2.7916   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472    1.2314   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.3703   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194    3.5175   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4249    3.6805    0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519    4.7911    0.8785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4145    2.5662    1.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670    1.4344    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9102   -0.0115   -0.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1996   -1.0923   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1457   -2.3466   -0.7640 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -2.8994   -0.7430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -3.2787   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -2.8365    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8829   -0.2282    1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8293    1.2247    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843    0.0068   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.3359    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3787    3.2355    0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8371    2.2754   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280    4.3713   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8804    2.7155    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620    0.6083    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9904    0.0095   -0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.0858   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704   -1.2140    0.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -2.3853   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9065   -2.7268    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -4.0039   -0.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8290   -3.6753    0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -4.1804   -0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765   -3.2983   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412   -3.1647    1.2131 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  8  3  1  0
 16 10  1  0
 22  5  1  0
 18  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Glaziovine, (+-)-isomer	MeSH

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.354

Monoisotopic Molecular Weight

297.136493476

IUPAC Name

11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

Traditional Name

11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3C(CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2

InChI Identifier

InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3

InChI Key

PNJUPRNTSWJWAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Proaporphines

Sub Class

Not Available

Direct Parent

Proaporphines

Alternative Parents

Substituents

Proaporphine
Tetrahydroisoquinoline
Indane
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Cyclic ketone
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organic oxygen 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)

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	1.86	ALOGPS
logP	2.31	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	7.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.79 m³·mol⁻¹	ChemAxon
Polarizability	32.25 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]+	176.349	30932474
DeepCCS	[M-H]-	173.991	30932474
DeepCCS	[M-2H]-	207.927	30932474
DeepCCS	[M+Na]+	183.153	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	174.6	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glaziovine	COC1=CC2=C3C(CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2	4004.1	Standard polar	33892256
Glaziovine	COC1=CC2=C3C(CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2	2627.8	Standard non polar	33892256
Glaziovine	COC1=CC2=C3C(CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2	2812.8	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 - Glaziovine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-0090000000-99112088c9bc21901de9	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glaziovine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glaziovine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glaziovine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Glaziovine 10V, Positive-QTOF	splash10-0002-0090000000-620f87966eb750d6f48d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glaziovine 20V, Positive-QTOF	splash10-00kb-0090000000-5975a668bc534ad56fc9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glaziovine 40V, Positive-QTOF	splash10-066u-2390000000-08ca20c3b3ffa0e7577f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glaziovine 10V, Negative-QTOF	splash10-0002-0090000000-f0a7b42101b1968126a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glaziovine 20V, Negative-QTOF	splash10-0002-0090000000-78a23744221062fedd98	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glaziovine 40V, Negative-QTOF	splash10-0006-2090000000-4f004bd2c5e6a1e3db4c	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65631

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 Glaziovine (HMDB0252740)

MOL for HMDB0252740 (Glaziovine)

3D MOL for HMDB0252740 (Glaziovine)

3D SDF for HMDB0252740 (Glaziovine)

3D-SDF for HMDB0252740 (Glaziovine)

PDB for HMDB0252740 (Glaziovine)

3D PDB for HMDB0252740 (Glaziovine)

SMILES for HMDB0252740 (Glaziovine)

INCHI for HMDB0252740 (Glaziovine)

Structure for HMDB0252740 (Glaziovine)

3D Structure for HMDB0252740 (Glaziovine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra