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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:46 UTC

Update Date

2021-09-14 15:15:54 UTC

HMDB ID

HMDB0041954

Secondary Accession Numbers

HMDB41954

Metabolite Identification

Common Name

Norbutorphanol

Description

Norcocaine belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. These are amino acids having a (-NH2) group attached to the beta carbon atom. Norcocaine is a very strong basic compound (based on its pKa).

Structure

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

HMDB0041954
     RDKit          3D
Norbutorphanol
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2666    1.7174    0.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698    0.8575   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.1246   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802   -0.9620   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.8504   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.1193    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737    0.9499    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    0.3369    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6371    1.7916    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    2.2348    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    1.7227   -1.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2330   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610   -0.4305   -0.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5025   -0.6217    0.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -1.8008   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2516   -1.7717   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -2.4663    0.7757 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -1.7744    1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -0.3116    1.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    2.5722   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946   -0.2027   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.7204   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903    1.7482    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493    2.1212    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    2.4022    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204    1.9580    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    3.3570    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.2264   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.1221   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -0.0253   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0767   -0.1259   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -1.3925    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156   -2.3960   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -2.8130   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -1.4505   -2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.1725    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -2.0127    2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -2.2124    2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -0.0393    2.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    0.2069    2.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 13  8  1  0
 16  5  1  0
 19  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  6
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv0541 09131211492D          

 20 23  0  0  0  0            999 V2000
    2.9923   -1.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1252   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5633   -2.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -3.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207   -1.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    0.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -2.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8127   -2.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9253   -3.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6184   -1.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634   -0.5574    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5820   -0.9250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7149   -0.1108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2444   -0.5581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817   -3.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    0.6047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.2013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  8  7  1  0  0  0  0
 11  3  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  6  0  0  0
 16  6  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 16 19  1  1  0  0  0
 14 20  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0041954

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO2/c18-12-4-3-11-9-14-16(19)6-2-1-5-15(16,7-8-17-14)13(11)10-12/h3-4,10,14,17-19H,1-2,5-9H2/t14-,15+,16-/m1/s1

> <INCHI_KEY>
GJOVVPXDEXUSTC-OWCLPIDISA-N

> <FORMULA>
C16H21NO2

> <MOLECULAR_WEIGHT>
259.3434

> <EXACT_MASS>
259.157228921

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.449695263202802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.6563468618380743

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.733400378285516

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.353508960896102

> <JCHEM_PKA_STRONGEST_BASIC>
9.495783677580592

> <JCHEM_POLAR_SURFACE_AREA>
52.489999999999995

> <JCHEM_REFRACTIVITY>
74.08330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041954
     RDKit          3D
Norbutorphanol
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2666    1.7174    0.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698    0.8575   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.1246   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802   -0.9620   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.8504   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.1193    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737    0.9499    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    0.3369    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6371    1.7916    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    2.2348    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    1.7227   -1.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2330   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610   -0.4305   -0.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5025   -0.6217    0.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -1.8008   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2516   -1.7717   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -2.4663    0.7757 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -1.7744    1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -0.3116    1.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    2.5722   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946   -0.2027   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.7204   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903    1.7482    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493    2.1212    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    2.4022    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204    1.9580    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    3.3570    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.2264   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.1221   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -0.0253   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0767   -0.1259   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -1.3925    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156   -2.3960   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -2.8130   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -1.4505   -2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.1725    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -2.0127    2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -2.2124    2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -0.0393    2.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    0.2069    2.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 13  8  1  0
 16  5  1  0
 19  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  6
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       5.586  -2.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.834  -0.637   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.051  -5.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.090  -6.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.145  -2.701   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.641   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.161  -1.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.219  -2.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.286  -2.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.060  -4.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.517  -3.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.594  -6.178   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.021  -3.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.172  -1.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.953  -1.727   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.201  -0.207   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.456  -1.042   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       4.633  -7.315   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.434   1.129   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       2.777   0.376   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4   11                                                       
CONECT    4    3   12                                                       
CONECT    5    1   15                                                       
CONECT    6    2   16                                                       
CONECT    7    8   15                                                       
CONECT    8    7   17                                                       
CONECT    9   11   14                                                       
CONECT   10   12   13                                                       
CONECT   11    3    9   13                                                  
CONECT   12    4   10   18                                                  
CONECT   13   10   11   15                                                  
CONECT   14    9   16   17   20                                             
CONECT   15    5    7   13   16                                             
CONECT   16    6   14   15   19                                             
CONECT   17    8   14                                                       
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0041954
HETATM    1  O1  UNL     1       4.267   1.717   0.432  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.270   0.857  -0.014  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.587  -0.125  -0.945  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.580  -0.962  -1.369  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.279  -0.850  -0.897  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.959   0.119   0.025  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.974   0.950   0.441  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.380   0.337   0.600  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.637   1.792   0.727  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.971   2.235   0.190  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.075   1.723  -1.231  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.013   0.233  -1.315  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.461  -0.431  -0.121  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.503  -0.622   0.801  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.879  -1.801  -0.383  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.252  -1.772  -1.387  1.00  0.00           C  
HETATM   17  N1  UNL     1      -0.462  -2.466   0.776  1.00  0.00           N  
HETATM   18  C15 UNL     1      -0.183  -1.774   1.947  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.343  -0.312   1.993  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.398   2.572  -0.093  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.595  -0.203  -1.304  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.825  -1.720  -2.088  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.790   1.748   1.176  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.549   2.121   1.787  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.137   2.402   0.176  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.820   1.958   0.815  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.932   3.357   0.112  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.303   2.226  -1.847  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.058   2.122  -1.621  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.516  -0.025  -2.279  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.077  -0.126  -1.449  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.029  -1.393   0.442  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.716  -2.396  -0.856  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.620  -2.813  -1.495  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.064  -1.451  -2.393  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.290  -3.172   0.518  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.876  -2.013   2.269  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.803  -2.212   2.787  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.338  -0.039   2.449  1.00  0.00           H  
HETATM   40  H21 UNL     1       0.415   0.207   2.625  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3    3    7
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   16
CONECT    6    7    7    8
CONECT    7   23
CONECT    8    9   13   19
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   17   33
CONECT   16   34   35
CONECT   17   18   36
CONECT   18   19   37   38
CONECT   19   39   40
END

HMDB0041954
     RDKit          3D
Norbutorphanol
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2666    1.7174    0.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2698    0.8575   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5870   -0.1246   -0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5802   -0.9620   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.8504   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.1193    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9737    0.9499    0.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    0.3369    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6371    1.7916    0.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709    2.2348    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    1.7227   -1.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127    0.2330   -1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4610   -0.4305   -0.1214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5025   -0.6217    0.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8790   -1.8008   -0.3834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2516   -1.7717   -1.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -2.4663    0.7757 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832   -1.7744    1.9471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3429   -0.3116    1.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978    2.5722   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5946   -0.2027   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8253   -1.7204   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903    1.7482    1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5493    2.1212    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    2.4022    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204    1.9580    0.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    3.3570    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.2264   -1.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0576    2.1221   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -0.0253   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0767   -0.1259   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0288   -1.3925    0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156   -2.3960   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204   -2.8130   -1.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640   -1.4505   -2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -3.1725    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8758   -2.0127    2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -2.2124    2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -0.0393    2.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    0.2069    2.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  7  2  1  0
 13  8  1  0
 16  5  1  0
 19  8  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  6
 16 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norbutorphanol	MeSH

Chemical Formula

C₁₆H₂₁NO₂

Average Molecular Weight

259.3434

Monoisotopic Molecular Weight

259.157228921

IUPAC Name

(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

Traditional Name

(1S,9R,10S)-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene-4,10-diol

CAS Registry Number

3792-68-5

SMILES

[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2

InChI Identifier

InChI=1S/C16H21NO2/c18-12-4-3-11-9-14-16(19)6-2-1-5-15(16,7-8-17-14)13(11)10-12/h3-4,10,14,17-19H,1-2,5-9H2/t14-,15+,16-/m1/s1

InChI Key

GJOVVPXDEXUSTC-OWCLPIDISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Piperidinecarboxylic acid
Tropane alkaloid
Phenoxy compound
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Pyrrolidine
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Secondary aliphatic amine
Carboxylic acid derivative
Secondary amine
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.55 g/L	ALOGPS
logP	1.4	ALOGPS
logP	1.66	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.35	ChemAxon
pKa (Strongest Basic)	9.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.08 m³·mol⁻¹	ChemAxon
Polarizability	28.45 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
DarkChem	[M+H]+	158.616	31661259
DarkChem	[M-H]-	156.98	31661259
DeepCCS	[M-2H]-	195.765	30932474
DeepCCS	[M+Na]+	170.93	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.5	32859911
AllCCS	[M-H]-	167.6	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norbutorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2	3657.0	Standard polar	33892256
Norbutorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2	2440.8	Standard non polar	33892256
Norbutorphanol	[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2	2494.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norbutorphanol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@@]4(CCCC[C@@]34O)C2=C1	2478.8	Semi standard non polar	33892256
Norbutorphanol,1TMS,isomer #2	C[Si](C)(C)O[C@@]12CCCC[C@@]13CCN[C@@H]2CC1=CC=C(O)C=C13	2433.2	Semi standard non polar	33892256
Norbutorphanol,1TMS,isomer #3	C[Si](C)(C)N1CC[C@]23CCCC[C@@]2(O)[C@H]1CC1=CC=C(O)C=C13	2450.8	Semi standard non polar	33892256
Norbutorphanol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@@]4(CCCC[C@@]34O[Si](C)(C)C)C2=C1	2425.3	Semi standard non polar	33892256
Norbutorphanol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C)CC[C@@]4(CCCC[C@@]34O)C2=C1	2430.8	Semi standard non polar	33892256
Norbutorphanol,2TMS,isomer #3	C[Si](C)(C)O[C@@]12CCCC[C@@]13CCN([Si](C)(C)C)[C@@H]2CC1=CC=C(O)C=C13	2399.1	Semi standard non polar	33892256
Norbutorphanol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C)C2=C1	2446.2	Semi standard non polar	33892256
Norbutorphanol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C)C2=C1	2611.3	Standard non polar	33892256
Norbutorphanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@@]4(CCCC[C@@]34O)C2=C1	2787.8	Semi standard non polar	33892256
Norbutorphanol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@]12CCCC[C@@]13CCN[C@@H]2CC1=CC=C(O)C=C13	2715.1	Semi standard non polar	33892256
Norbutorphanol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1CC[C@]23CCCC[C@@]2(O)[C@H]1CC1=CC=C(O)C=C13	2682.1	Semi standard non polar	33892256
Norbutorphanol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@@]4(CCCC[C@@]34O[Si](C)(C)C(C)(C)C)C2=C1	2893.9	Semi standard non polar	33892256
Norbutorphanol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C(C)(C)C)CC[C@@]4(CCCC[C@@]34O)C2=C1	2892.7	Semi standard non polar	33892256
Norbutorphanol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@]12CCCC[C@@]13CCN([Si](C)(C)C(C)(C)C)[C@@H]2CC1=CC=C(O)C=C13	2864.9	Semi standard non polar	33892256
Norbutorphanol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C(C)(C)C)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C(C)(C)C)C2=C1	3114.4	Semi standard non polar	33892256
Norbutorphanol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3N([Si](C)(C)C(C)(C)C)CC[C@@]4(CCCC[C@@]34O[Si](C)(C)C(C)(C)C)C2=C1	3337.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l6-3090000000-86580687a4b5d9a2ced3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (2 TMS) - 70eV, Positive	splash10-00a9-2009000000-7d2923e87bb3c217669f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norbutorphanol GC-MS ("Norbutorphanol,1TMS,#2" TMS) - 70eV, Positive	Not Available	2021-10-14	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 - Norbutorphanol 10V, Positive-QTOF	splash10-01ox-0090000000-c766d71bab5da602ca9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 20V, Positive-QTOF	splash10-0006-0090000000-e3b6d582fc7e66b4225d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 40V, Positive-QTOF	splash10-0pb9-9130000000-8d010108007271303fc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 10V, Negative-QTOF	splash10-0a4i-0090000000-6c4d47fa09baffac3e45	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 20V, Negative-QTOF	splash10-0a4l-0090000000-24708a73c43829827e5d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 40V, Negative-QTOF	splash10-01ox-0090000000-5cb105e308f9c850395f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 10V, Positive-QTOF	splash10-03di-0090000000-8afd14fe90123d0498ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 20V, Positive-QTOF	splash10-03di-0090000000-3d36e1805424920c0620	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 40V, Positive-QTOF	splash10-0006-6590000000-442ac7c5f5d3ec3f60aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 10V, Negative-QTOF	splash10-0a4i-0090000000-04dd86dfd4af8c885642	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 20V, Negative-QTOF	splash10-0a4i-0090000000-04dd86dfd4af8c885642	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norbutorphanol 40V, Negative-QTOF	splash10-0a4i-0790000000-236c9c662b1d1f699661	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

Chemspider ID

27185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norcocaine

METLIN ID

Not Available

PubChem Compound

29230

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 Norbutorphanol (HMDB0041954)

MOL for HMDB0041954 (Norbutorphanol)

3D MOL for HMDB0041954 (Norbutorphanol)

3D SDF for HMDB0041954 (Norbutorphanol)

3D-SDF for HMDB0041954 (Norbutorphanol)

PDB for HMDB0041954 (Norbutorphanol)

3D PDB for HMDB0041954 (Norbutorphanol)

SMILES for HMDB0041954 (Norbutorphanol)

INCHI for HMDB0041954 (Norbutorphanol)

Structure for HMDB0041954 (Norbutorphanol)

3D Structure for HMDB0041954 (Norbutorphanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra