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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:50:03 UTC

Update Date

2021-09-14 15:19:57 UTC

HMDB ID

HMDB0041959

Secondary Accession Numbers

HMDB41959

Metabolite Identification

Common Name

Normorphine

Description

Normorphine, also known as desmethylmorphine, 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. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. Normorphine is a very strong basic compound (based on its pKa). Its formation from morphine is catalyzed by the liver enzymes CYP3A4 and CYP2C8. Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States, it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity.

Structure

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

HMDB0041959
     RDKit          3D
Normorphine
 37 41  0  0  0  0  0  0  0  0999 V2000
    4.3122   -0.0698   -0.2147 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5925   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -1.7663   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229   -2.2836   -1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4593   -1.6080   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -0.4706    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    0.0944    0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898    1.2430    0.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    1.6507    0.8780 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2955    2.6084   -0.2611 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5089    3.2083   -0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3045    2.0578   -1.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    1.0183   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.3731   -0.2204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9438   -1.0429   -0.3562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9423   -2.0574   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -1.4122    0.8739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.6312    2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094   -0.2951    1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    0.3616    0.6977 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5057    0.7759    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6723   -2.2649   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -3.1845   -1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793    2.0924    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    3.4517    0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    4.0473   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439    2.5569   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.7076   -2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    0.9468    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373   -1.0252   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -2.4426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -2.9537   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -1.2992    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.2888    2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488   -1.2548    2.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149    0.4046    2.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.2334    2.1542 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  1
  7  2  1  0
 20  9  1  0
 16  5  1  0
 20  6  1  0
 20 14  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  1
 10 25  1  1
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END


  Mrv1652303062020512D          

 23 27  0  0  0  0            999 V2000
10002.0519 9998.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9723 9998.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9356 9998.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.825710001.2442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.825710001.8429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998910001.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.002010000.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.412810000.2987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.8257 9998.1770    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.349610000.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9370 9999.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3495 9998.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1745 9998.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.412710001.1344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.587710001.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.175110000.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5877 9999.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4127 9999.7053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.825210000.4199    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.651110000.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8261 9998.9958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.6510 9998.9957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.0636 9999.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12  3  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22  1  1  6  0  0  0
 21  9  1  1  0  0  0
 14  8  1  6  0  0  0
 16 10  2  0  0  0  0
 13 17  2  0  0  0  0
 20 19  1  0  0  0  0
 19  4  1  1  0  0  0
 18 21  1  0  0  0  0
 13  2  1  0  0  0  0
  2 21  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  5 14  1  0  0  0  0
 18  7  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041959

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1

> <INCHI_KEY>
ONBWJWYUHXVEJS-ZTYRTETDSA-N

> <FORMULA>
C16H17NO3

> <MOLECULAR_WEIGHT>
271.316

> <EXACT_MASS>
271.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.750768535208948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
0.26351152929242355

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.783197012081622

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.472726017083646

> <JCHEM_PKA_STRONGEST_BASIC>
9.77437278618805

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
74.8277

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041959
     RDKit          3D
Normorphine
 37 41  0  0  0  0  0  0  0  0999 V2000
    4.3122   -0.0698   -0.2147 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5925   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -1.7663   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229   -2.2836   -1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4593   -1.6080   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -0.4706    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    0.0944    0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898    1.2430    0.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    1.6507    0.8780 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2955    2.6084   -0.2611 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5089    3.2083   -0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3045    2.0578   -1.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    1.0183   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.3731   -0.2204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9438   -1.0429   -0.3562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9423   -2.0574   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -1.4122    0.8739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.6312    2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094   -0.2951    1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    0.3616    0.6977 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5057    0.7759    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6723   -2.2649   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -3.1845   -1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793    2.0924    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    3.4517    0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    4.0473   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439    2.5569   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.7076   -2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    0.9468    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373   -1.0252   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -2.4426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -2.9537   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -1.2992    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.2888    2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488   -1.2548    2.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149    0.4046    2.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.2334    2.1542 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  1
  7  2  1  0
 20  9  1  0
 16  5  1  0
 20  6  1  0
 20 14  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  1
 10 25  1  1
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  O   UNK     0    8670.4978663.459   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8666.6158663.742   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8662.8138663.470   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8668.2088668.989   0.000  0.00  0.00           H+0
HETATM    5  N   UNK     0    8668.2088670.107   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8666.6658670.107   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8666.6708667.459   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0    8667.4378667.224   0.000  0.00  0.00           H+0
HETATM    9  H   UNK     0    8668.2088663.264   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8663.5868667.460   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.8168666.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.5868664.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.1268664.792   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.4378668.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.8978668.784   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.1278667.450   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.8978666.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.4378666.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.2078667.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.7498667.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.2098664.792   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.7498664.792   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.5198666.126   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2   13   21                                                       
CONECT    3   12                                                            
CONECT    4   19                                                            
CONECT    5    6   14                                                       
CONECT    6    5    7                                                       
CONECT    7    6   18                                                       
CONECT    8   14                                                            
CONECT    9   21                                                            
CONECT   10   11   16                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    3                                                  
CONECT   13   12   17    2                                                  
CONECT   14   15   19    8    5                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   10                                                  
CONECT   17   16   18   13                                                  
CONECT   18   17   19   21    7                                             
CONECT   19   14   18   20    4                                             
CONECT   20   23   19                                                       
CONECT   21   22    9   18    2                                             
CONECT   22   21   23    1                                                  
CONECT   23   20   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0041959
HETATM    1  O1  UNL     1       4.312  -0.070  -0.215  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.035  -0.592  -0.365  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.819  -1.766  -1.070  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.523  -2.284  -1.214  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.459  -1.608  -0.644  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.744  -0.471   0.029  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.959   0.094   0.214  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.790   1.243   0.955  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.410   1.651   0.878  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.296   2.608  -0.261  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.509   3.208  -0.585  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.305   2.058  -1.474  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.125   1.018  -1.482  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.461   0.373  -0.220  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.944  -1.043  -0.356  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.942  -2.057  -0.736  1.00  0.00           C  
HETATM   17  N1  UNL     1      -2.594  -1.412   0.874  1.00  0.00           N  
HETATM   18  C14 UNL     1      -2.166  -0.631   2.004  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.709  -0.295   1.984  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.274   0.362   0.698  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.506   0.776   0.288  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.672  -2.265  -1.500  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.352  -3.184  -1.755  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.179   2.092   1.868  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.370   3.452   0.089  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.412   4.047  -1.067  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.044   2.557  -2.429  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.504   0.708  -2.466  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.268   0.947   0.284  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.737  -1.025  -1.161  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.079  -2.443  -1.788  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.043  -2.954  -0.089  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.630  -1.299   0.798  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.787   0.289   2.159  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.349  -1.255   2.914  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.515   0.405   2.826  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.130  -1.233   2.154  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   16
CONECT    6    7    7   20
CONECT    7    8
CONECT    8    9
CONECT    9   10   20   24
CONECT   10   11   12   25
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   20   29
CONECT   15   16   17   30
CONECT   16   31   32
CONECT   17   18   33
CONECT   18   19   34   35
CONECT   19   20   36   37
END

HMDB0041959
     RDKit          3D
Normorphine
 37 41  0  0  0  0  0  0  0  0999 V2000
    4.3122   -0.0698   -0.2147 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347   -0.5925   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8189   -1.7663   -1.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229   -2.2836   -1.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4593   -1.6080   -0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7442   -0.4706    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    0.0944    0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898    1.2430    0.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    1.6507    0.8780 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2955    2.6084   -0.2611 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5089    3.2083   -0.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3045    2.0578   -1.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    1.0183   -1.4823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.3731   -0.2204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9438   -1.0429   -0.3562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9423   -2.0574   -0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -1.4122    0.8739 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655   -0.6312    2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7094   -0.2951    1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743    0.3616    0.6977 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5057    0.7759    0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6723   -2.2649   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -3.1845   -1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793    2.0924    1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3696    3.4517    0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4116    4.0473   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439    2.5569   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044    0.7076   -2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2680    0.9468    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373   -1.0252   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -2.4426   -1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -2.9537   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6300   -1.2992    0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7865    0.2888    2.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488   -1.2548    2.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149    0.4046    2.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303   -1.2334    2.1542 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  1
  7  2  1  0
 20  9  1  0
 16  5  1  0
 20  6  1  0
 20 14  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  9 24  1  1
 10 25  1  1
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  1
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desmethylmorphine	HMDB
Normorphine perchlorate	HMDB
N-Demethylmorphine	HMDB
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol hydrochloride	HMDB
4,5-Epoxy-3,6-dihydroxymorphin-7-ene	HMDB
Normorphine hydrochloride	HMDB
Normorphine sulfamate	HMDB
(-)-Normorphine	HMDB
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol	HMDB
(5Α,6α)-7,8-didehydro-4,5-epoxymorphinan-3,6-diol	HMDB
4,5-Epoxy-3,6-dihydromorphin-7-ene	HMDB
Demethylmorphine	HMDB
N-Normorphine	HMDB
Normorphine	HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Molecular Weight

271.316

Monoisotopic Molecular Weight

271.120843411

IUPAC Name

(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol

Traditional Name

(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol

CAS Registry Number

466-97-7

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O

InChI Identifier

InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1

InChI Key

ONBWJWYUHXVEJS-ZTYRTETDSA-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
Aralkylamine
Piperidine
Benzenoid
Secondary alcohol
Secondary aliphatic amine
Ether
Oxacycle
Secondary amine
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:7633 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	273 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.17	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.19 g/L	ALOGPS
logP	0.4	ALOGPS
logP	0.26	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.47	ChemAxon
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.83 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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
DeepCCS	[M-2H]-	202.487	30932474
DeepCCS	[M+Na]+	178.719	30932474
AllCCS	[M+H]+	164.8	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	168.1	32859911
AllCCS	[M+Na]+	169.0	32859911
AllCCS	[M-H]-	168.7	32859911
AllCCS	[M+Na-2H]-	168.0	32859911
AllCCS	[M+HCOO]-	167.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.61 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6377 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	146.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1043.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	110.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	274.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	280.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	570.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	674.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	280.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	839.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	199.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	475.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	398.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	128.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Normorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O	3787.2	Standard polar	33892256
Normorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O	2423.1	Standard non polar	33892256
Normorphine	[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O	2488.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Normorphine,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O5	2467.3	Semi standard non polar	33892256
Normorphine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]35	2503.2	Semi standard non polar	33892256
Normorphine,1TMS,isomer #3	C[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5	2500.7	Semi standard non polar	33892256
Normorphine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)C=C[C@@H]35	2507.3	Semi standard non polar	33892256
Normorphine,2TMS,isomer #2	C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C)[C@H]1O5	2500.5	Semi standard non polar	33892256
Normorphine,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2507.8	Semi standard non polar	33892256
Normorphine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2537.1	Semi standard non polar	33892256
Normorphine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2646.5	Standard non polar	33892256
Normorphine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O5	2746.0	Semi standard non polar	33892256
Normorphine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]35	2775.7	Semi standard non polar	33892256
Normorphine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5	2722.9	Semi standard non polar	33892256
Normorphine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@@H]35	2990.2	Semi standard non polar	33892256
Normorphine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C(C)(C)C)[C@H]1O5	2957.8	Semi standard non polar	33892256
Normorphine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	2960.0	Semi standard non polar	33892256
Normorphine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	3235.5	Semi standard non polar	33892256
Normorphine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	3323.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Normorphine 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 - Normorphine 10V, Positive-QTOF	splash10-00di-0090000000-0ce88f6c7aacd22857e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normorphine 20V, Positive-QTOF	splash10-00di-0090000000-c13b47c233a54b20d3a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normorphine 40V, Positive-QTOF	splash10-00di-0090000000-e760b6a34c0df4dae8c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normorphine 10V, Negative-QTOF	splash10-00di-0090000000-19dbfadd3d4c17868278	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normorphine 20V, Negative-QTOF	splash10-00di-0090000000-19dbfadd3d4c17868278	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normorphine 40V, Negative-QTOF	splash10-01b9-0090000000-d773172bb6e200eaed9a	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Morphine Action Pathway		Not Available
Morphine Metabolism Pathway		Not Available

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

4575435

KEGG Compound ID

C11785

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Normorphine

METLIN ID

Not Available

PubChem Compound

5462508

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 Normorphine (HMDB0041959)

MOL for HMDB0041959 (Normorphine)

3D MOL for HMDB0041959 (Normorphine)

3D SDF for HMDB0041959 (Normorphine)

3D-SDF for HMDB0041959 (Normorphine)

PDB for HMDB0041959 (Normorphine)

3D PDB for HMDB0041959 (Normorphine)

SMILES for HMDB0041959 (Normorphine)

INCHI for HMDB0041959 (Normorphine)

Structure for HMDB0041959 (Normorphine)

3D Structure for HMDB0041959 (Normorphine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra