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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:05 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029382

Secondary Accession Numbers

HMDB29382

Metabolite Identification

Common Name

Genomorphine

Description

Genomorphine belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review very few articles have been published on Genomorphine.

Structure

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

HMDB0029382
     RDKit          3D
Genomorphine
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.8271    0.6268   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    0.0265   -0.5877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7004   -1.2555   -0.9891 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6885    0.6729   -1.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -0.2005   -1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -0.6202   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    0.5527   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313    1.4687    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    2.5311    1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    2.5908    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.6145    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    1.6808   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    0.5414   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -0.6168   -1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -1.5380   -0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489   -2.4615    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -2.7085    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -2.0240    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -1.3699    1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -1.0897    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.0134    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130    1.3245    1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    0.8383   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4966   -0.0909    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    1.5406    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.7037   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7272   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1037   -2.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    0.2805   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    3.2990    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    3.4121    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.9664   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -2.1126   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238   -3.4354   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -3.6682    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717   -2.2479    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -1.0309    2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -2.0002    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -0.3950    1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    2.1763    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669    1.4077    2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 15  6  1  0
 20  6  1  0
 13  7  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv0541 02241219112D          

 22 26  0  0  0  0            999 V2000
   -2.1011    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7759   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3644   -0.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6118    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845    2.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0382    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7805    2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1845   -2.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -0.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  7 22  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029382

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1(=O)CCC23C4OC5=C(O)C=CC(CC1C2C=CC4O)=C35

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3

> <INCHI_KEY>
AMAPEXTUMXQULJ-UHFFFAOYSA-N

> <FORMULA>
C17H19NO4

> <MOLECULAR_WEIGHT>
301.3371

> <EXACT_MASS>
301.131408101

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.496275733663836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,14-dihydroxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
0.07268204366666614

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.782766070986089

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.807915086668054

> <JCHEM_PKA_STRONGEST_BASIC>
2.74930407843556

> <JCHEM_POLAR_SURFACE_AREA>
76.57

> <JCHEM_REFRACTIVITY>
82.1673

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dihydroxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029382
     RDKit          3D
Genomorphine
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.8271    0.6268   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    0.0265   -0.5877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7004   -1.2555   -0.9891 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6885    0.6729   -1.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -0.2005   -1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -0.6202   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    0.5527   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313    1.4687    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    2.5311    1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    2.5908    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.6145    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    1.6808   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    0.5414   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -0.6168   -1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -1.5380   -0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489   -2.4615    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -2.7085    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -2.0240    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -1.3699    1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -1.0897    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.0134    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130    1.3245    1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    0.8383   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4966   -0.0909    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    1.5406    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.7037   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7272   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1037   -2.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    0.2805   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    3.2990    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    3.4121    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.9664   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -2.1126   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238   -3.4354   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -3.6682    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717   -2.2479    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -1.0309    2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -2.0002    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -0.3950    1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    2.1763    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669    1.4077    2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 15  6  1  0
 20  6  1  0
 13  7  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  CHG  2   2   1   3  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -3.922   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.689  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.689  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.457  -3.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.071  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.315  -2.925   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.547  -1.539   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.009   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.071   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.457  -0.768   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071  -1.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.161  -0.768   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.161   0.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.078   3.851   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.689   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.689   1.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.457   0.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.071   1.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.071   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.457   3.851   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.078  -3.851   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.078  -1.130   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4   11                                                       
CONECT    6    7                                                            
CONECT    7    6    8   12   22                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   11   17                                             
CONECT   11    5   10   12                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   18                                                       
CONECT   14   15                                                            
CONECT   15   14   16   20                                                  
CONECT   16    1   15   17                                                  
CONECT   17   10   16   18                                                  
CONECT   18   13   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19                                                       
CONECT   21    3                                                            
CONECT   22    7                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0029382
HETATM    1  C1  UNL     1      -3.827   0.627  -0.462  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.540   0.027  -0.588  1.00  0.00           N1+
HETATM    3  O1  UNL     1      -2.700  -1.255  -0.989  1.00  0.00           O1-
HETATM    4  C2  UNL     1      -1.689   0.673  -1.585  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.519  -0.200  -1.871  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.189  -0.620  -0.636  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.890   0.553  -0.053  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.231   1.469   0.680  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.964   2.531   1.155  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.331   2.591   0.851  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.945   1.615   0.095  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.297   1.681  -0.199  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.209   0.541  -0.385  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.461  -0.617  -1.154  1.00  0.00           O  
HETATM   15  C11 UNL     1       1.353  -1.538  -0.904  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.649  -2.461   0.230  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.025  -2.709   0.313  1.00  0.00           O  
HETATM   18  C13 UNL     1       1.171  -2.024   1.560  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.032  -1.370   1.668  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.740  -1.090   0.439  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.786  -0.013   0.659  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.213   1.325   1.011  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.218   0.838  -1.464  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.497  -0.091   0.050  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.766   1.541   0.162  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.445   1.704  -1.321  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.323   0.727  -2.516  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.913  -1.104  -2.421  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.168   0.280  -2.597  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.481   3.299   1.750  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.916   3.412   1.213  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.741   0.966  -0.751  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.252  -2.113  -1.832  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.124  -3.435  -0.011  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.138  -3.668   0.534  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.772  -2.248   2.462  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.357  -1.031   2.623  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.257  -2.000   0.080  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.481  -0.395   1.435  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.800   2.176   0.632  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.267   1.408   2.137  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   21
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   15   20
CONECT    7    8    8   13
CONECT    8    9   22
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   13   13
CONECT   12   32
CONECT   13   14
CONECT   14   15
CONECT   15   16   33
CONECT   16   17   18   34
CONECT   17   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   38
CONECT   21   22   39
CONECT   22   40   41
END

HMDB0029382
     RDKit          3D
Genomorphine
 41 45  0  0  0  0  0  0  0  0999 V2000
   -3.8271    0.6268   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5403    0.0265   -0.5877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7004   -1.2555   -0.9891 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6885    0.6729   -1.5852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -0.2005   -1.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -0.6202   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    0.5527   -0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313    1.4687    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    2.5311    1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    2.5908    0.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.6145    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966    1.6808   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2087    0.5414   -0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4607   -0.6168   -1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3533   -1.5380   -0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489   -2.4615    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -2.7085    0.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -2.0240    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -1.3699    1.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401   -1.0897    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.0134    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2130    1.3245    1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2178    0.8383   -1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4966   -0.0909    0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7657    1.5406    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.7037   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7272   -2.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1037   -2.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1683    0.2805   -2.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    3.2990    1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    3.4121    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.9664   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -2.1126   -1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1238   -3.4354   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377   -3.6682    0.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7717   -2.2479    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -1.0309    2.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -2.0002    0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806   -0.3950    1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7997    2.1763    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2669    1.4077    2.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  2  1  0
 15  6  1  0
 20  6  1  0
 13  7  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  CHG  2   2   1   3  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Genomorphin	HMDB
Heterocodeine	HMDB
Morphine N-oxide	HMDB
Morphine oxide	HMDB
Morphine-N-oxide	HMDB

Chemical Formula

C₁₇H₁₉NO₄

Average Molecular Weight

301.3371

Monoisotopic Molecular Weight

301.131408101

IUPAC Name

10,14-dihydroxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

Traditional Name

10,14-dihydroxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

CAS Registry Number

639-46-3

SMILES

CN1(=O)CCC23C4OC5=C(O)C=CC(CC1C2C=CC4O)=C35

InChI Identifier

InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3

InChI Key

AMAPEXTUMXQULJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Piperidine
Trialkyl amine oxide
Secondary alcohol
N-oxide
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Alcohol
Organic zwitterion
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:7002 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029382)
Cytoplasm (HMDB: HMDB0029382)

Source

Endogenous

Endogenous (HMDB: HMDB0029382)

Exogenous

Food

Food (HMDB: HMDB0029382)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	272 - 273 °C	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	0.51 g/L	ALOGPS
logP	-0.03	ALOGPS
logP	0.073	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.57 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.17 m³·mol⁻¹	ChemAxon
Polarizability	30.5 Å³	ChemAxon
Number of Rings	5	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
DarkChem	[M+H]+	168.601	31661259
DarkChem	[M-H]-	165.176	31661259
DeepCCS	[M-2H]-	197.75	30932474
DeepCCS	[M+Na]+	172.977	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.0	32859911
AllCCS	[M+HCOO]-	174.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Genomorphine	CN1(=O)CCC23C4OC5=C(O)C=CC(CC1C2C=CC4O)=C35	3819.4	Standard polar	33892256
Genomorphine	CN1(=O)CCC23C4OC5=C(O)C=CC(CC1C2C=CC4O)=C35	2220.7	Standard non polar	33892256
Genomorphine	CN1(=O)CCC23C4OC5=C(O)C=CC(CC1C2C=CC4O)=C35	2551.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Genomorphine,1TMS,isomer #1	C[N+]1([O-])CCC23C4=C5C=CC(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C5	2625.2	Semi standard non polar	33892256
Genomorphine,1TMS,isomer #2	C[N+]1([O-])CCC23C4=C5C=CC(O)=C4OC2C(O[Si](C)(C)C)C=CC3C1C5	2595.2	Semi standard non polar	33892256
Genomorphine,2TMS,isomer #1	C[N+]1([O-])CCC23C4=C5C=CC(O[Si](C)(C)C)=C4OC2C(O[Si](C)(C)C)C=CC3C1C5	2629.6	Semi standard non polar	33892256
Genomorphine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2CC3C4C=CC(O)C5OC1=C2C45CC[N+]3(C)[O-]	2900.7	Semi standard non polar	33892256
Genomorphine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=CC2C3CC4=CC=C(O)C5=C4C2(CC[N+]3(C)[O-])C1O5	2840.1	Semi standard non polar	33892256
Genomorphine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2CC3C4C=CC(O[Si](C)(C)C(C)(C)C)C5OC1=C2C45CC[N+]3(C)[O-]	3128.3	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 - Genomorphine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pcc-3091000000-22168af88abd6004ec10	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genomorphine GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-5109600000-83ddd0bb3c6a80350733	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Genomorphine 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 - Genomorphine 10V, Positive-QTOF	splash10-0udi-0029000000-53443eefb3724d6a20f8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 20V, Positive-QTOF	splash10-0udi-0093000000-80e5135fca639e328d85	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 40V, Positive-QTOF	splash10-0f7d-0390000000-c91aff023c4a2a96ef75	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 10V, Negative-QTOF	splash10-0udi-0009000000-ddb4f06d67be77be239e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 20V, Negative-QTOF	splash10-0udi-0009000000-e921cb9736277a8287d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 40V, Negative-QTOF	splash10-0ufr-5395000000-84ad71f493e5448d04e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 10V, Positive-QTOF	splash10-0udi-0009000000-ab6f6c1d45a17ba966cd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 20V, Positive-QTOF	splash10-0f89-0096000000-13d01af587f3aa2b55f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 40V, Positive-QTOF	splash10-0zi0-2093000000-465bb1490118e1ab372d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 10V, Negative-QTOF	splash10-0udi-0009000000-867b26b8e9b8bd5f9273	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 20V, Negative-QTOF	splash10-0udi-0009000000-867b26b8e9b8bd5f9273	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Genomorphine 40V, Negative-QTOF	splash10-0udi-0009000000-867b26b8e9b8bd5f9273	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

C00057481

Chemspider ID

4515047

KEGG Compound ID

C11786

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Morphine-N-oxide

METLIN ID

Not Available

PubChem Compound

5362459

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Genomorphine (HMDB0029382)

MOL for HMDB0029382 (Genomorphine)

3D MOL for HMDB0029382 (Genomorphine)

3D SDF for HMDB0029382 (Genomorphine)

3D-SDF for HMDB0029382 (Genomorphine)

PDB for HMDB0029382 (Genomorphine)

3D PDB for HMDB0029382 (Genomorphine)

SMILES for HMDB0029382 (Genomorphine)

INCHI for HMDB0029382 (Genomorphine)

Structure for HMDB0029382 (Genomorphine)

3D Structure for HMDB0029382 (Genomorphine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra