Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:49:52 UTC

Update Date

2022-03-07 02:57:14 UTC

HMDB ID

HMDB0041956

Secondary Accession Numbers

HMDB41956

Metabolite Identification

Common Name

Nordihydrocodeine

Description

Nordihydrocodeine 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 a significant number of articles have been published on Nordihydrocodeine.

Structure

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

HMDB0041956
     RDKit          3D
Nordihydrocodeine
 42 46  0  0  0  0  0  0  0  0999 V2000
    5.3386   -0.0401   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    0.4410   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -0.2545   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515   -1.5185   -0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.1790   -0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -1.6008   -0.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -0.3597    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7207    0.3380    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3753    1.5422    0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    1.7303    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5255    2.6205   -0.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0032    2.4442   -1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470    2.6097   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    1.2321   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726    0.2317   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.2176   -0.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8821   -2.1880   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.3801    0.6452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -1.3824    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -0.2485    1.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    0.3665    0.5883 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8517   -0.6138    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732    0.8675   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.6145   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -1.9814   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -3.1613   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.1298    1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    3.6874    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    2.6305   -2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    3.3565   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    2.9853    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771    0.9694    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.2480   -1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    0.3515   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -1.3642   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -2.9993    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8827   -2.7278   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638   -2.1556    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -2.3589    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -1.2934    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -0.6392    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    0.4963    2.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

  Mrv0541 06301311492D          

 22 26  0  0  0  0            999 V2000
    3.9720    3.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3629    1.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761    1.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748    1.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6722    1.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217    0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2453    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5425    0.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353    0.1772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1305    2.4445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1563    2.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261    1.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3142    2.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474    2.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1532    1.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8975   -0.4067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784    3.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707    3.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071    2.7799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.5708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  2  0  0  0  0
  7  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17  6  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  1  0  0  0
 17 16  1  0  0  0  0
 18  7  1  0  0  0  0
 18 11  1  0  0  0  0
 12 19  1  6  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  1  0  0  0  0
 11 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0041956

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC3=C4C(OC5[C@@H](O)CCC1[C@@]45CCN2)=C(OC)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2,5,10-12,16,18-19H,3-4,6-8H2,1H3/t10?,11-,12+,16?,17+/m1/s1

> <INCHI_KEY>
IKGNKASQBMZRJL-YGJOGQJWSA-N

> <FORMULA>
C17H21NO3

> <MOLECULAR_WEIGHT>
287.3535

> <EXACT_MASS>
287.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.62683645249522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,14S)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.1659175423333341

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.151589917219553

> <JCHEM_PKA_STRONGEST_BASIC>
10.16496420547849

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
78.3474

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,14S)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041956
     RDKit          3D
Nordihydrocodeine
 42 46  0  0  0  0  0  0  0  0999 V2000
    5.3386   -0.0401   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    0.4410   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -0.2545   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515   -1.5185   -0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.1790   -0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -1.6008   -0.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -0.3597    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7207    0.3380    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3753    1.5422    0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    1.7303    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5255    2.6205   -0.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0032    2.4442   -1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470    2.6097   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    1.2321   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726    0.2317   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.2176   -0.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8821   -2.1880   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.3801    0.6452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -1.3824    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -0.2485    1.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    0.3665    0.5883 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8517   -0.6138    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732    0.8675   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.6145   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -1.9814   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -3.1613   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.1298    1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    3.6874    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    2.6305   -2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    3.3565   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    2.9853    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771    0.9694    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.2480   -1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    0.3515   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -1.3642   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -2.9993    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8827   -2.7278   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638   -2.1556    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -2.3589    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -1.2934    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -0.6392    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    0.4963    2.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 30-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-13         0                                  
HETATM    1  C   UNK     0       7.414   7.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.144   1.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.635   2.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.073   3.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.721   3.328   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.467   1.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.200  -0.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.058   0.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.613   1.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.437   1.797   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.546   0.331   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.110   4.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.758   4.545   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.649   2.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.187   4.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.635   4.259   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.019   2.701   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.542  -0.759   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.640   6.019   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.345   5.959   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.867   5.189   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       5.172  -1.065   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2    5    9                                                       
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    2   13                                                       
CONECT    6    7   17                                                       
CONECT    7    6   18                                                       
CONECT    8    9   11                                                       
CONECT    9    2    8   14                                                  
CONECT   10    3   11   17                                                  
CONECT   11    8   10   18   22                                             
CONECT   12    4   16   19                                                  
CONECT   13    5   15   20                                                  
CONECT   14    9   15   17                                                  
CONECT   15   13   14   21                                                  
CONECT   16   12   17   21                                                  
CONECT   17    6   10   14   16                                             
CONECT   18    7   11                                                       
CONECT   19   12                                                            
CONECT   20    1   13                                                       
CONECT   21   15   16                                                       
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0041956
HETATM    1  C1  UNL     1       5.339  -0.040  -0.398  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.080   0.441  -0.006  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.898  -0.255  -0.185  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.851  -1.519  -0.781  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.623  -2.179  -0.938  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.465  -1.601  -0.513  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.579  -0.360   0.066  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.721   0.338   0.249  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.375   1.542   0.863  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.022   1.730   0.779  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.525   2.621  -0.278  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.003   2.444  -1.537  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.047   2.610  -0.234  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.640   1.232  -0.421  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.573   0.232  -0.556  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.007  -1.218  -0.558  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.882  -2.188  -0.655  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.799  -1.380   0.645  1.00  0.00           N  
HETATM   19  C15 UNL     1      -1.959  -1.382   1.802  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.016  -0.249   1.875  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.618   0.367   0.588  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.852  -0.614   0.415  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.973   0.868  -0.604  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.272  -0.614  -1.328  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.768  -1.981  -1.120  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.567  -3.161  -1.400  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.367   2.130   1.765  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.261   3.687   0.005  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.653   2.630  -2.266  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.481   3.356  -0.932  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.309   2.985   0.800  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.277   0.969   0.456  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.333   1.248  -1.307  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.992   0.352  -1.508  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.683  -1.364  -1.426  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.034  -2.999   0.080  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.883  -2.728  -1.652  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.464  -2.156   0.614  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.429  -2.359   1.939  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.675  -1.293   2.682  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.061  -0.639   2.351  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.371   0.496   2.630  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   17
CONECT    7    8    8   21
CONECT    8    9
CONECT    9   10
CONECT   10   11   21   27
CONECT   11   12   13   28
CONECT   12   29
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   21   34
CONECT   16   17   18   35
CONECT   17   36   37
CONECT   18   19   38
CONECT   19   20   39   40
CONECT   20   21   41   42
END

HMDB0041956
     RDKit          3D
Nordihydrocodeine
 42 46  0  0  0  0  0  0  0  0999 V2000
    5.3386   -0.0401   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0801    0.4410   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8981   -0.2545   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8515   -1.5185   -0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.1790   -0.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649   -1.6008   -0.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -0.3597    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7207    0.3380    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3753    1.5422    0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    1.7303    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5255    2.6205   -0.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0032    2.4442   -1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470    2.6097   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404    1.2321   -0.4209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726    0.2317   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0073   -1.2176   -0.5585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8821   -2.1880   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.3801    0.6452 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -1.3824    1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0156   -0.2485    1.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    0.3665    0.5883 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8517   -0.6138    0.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9732    0.8675   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.6145   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -1.9814   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5673   -3.1613   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    2.1298    1.7653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2611    3.6874    0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6533    2.6305   -2.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4806    3.3565   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3087    2.9853    0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2771    0.9694    0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3331    1.2480   -1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    0.3515   -1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6831   -1.3642   -1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0336   -2.9993    0.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8827   -2.7278   -1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638   -2.1556    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4285   -2.3589    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6754   -1.2934    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -0.6392    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708    0.4963    2.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nordihydrocodeine	MeSH

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

(1S,5R,14S)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol

Traditional Name

(1S,5R,14S)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C4C(OC5[C@@H](O)CCC1[C@@]45CCN2)=C(OC)C=C3

InChI Identifier

InChI=1S/C17H21NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2,5,10-12,16,18-19H,3-4,6-8H2,1H3/t10?,11-,12+,16?,17+/m1/s1

InChI Key

IKGNKASQBMZRJL-YGJOGQJWSA-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
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Cyclic alcohol
Secondary alcohol
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0041956)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.56 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.17	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.15	ChemAxon
pKa (Strongest Basic)	10.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.35 m³·mol⁻¹	ChemAxon
Polarizability	30.63 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]+	166.486	31661259
DarkChem	[M-H]-	162.351	31661259
DeepCCS	[M-2H]-	210.309	30932474
DeepCCS	[M+Na]+	185.385	30932474
AllCCS	[M+H]+	169.5	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	172.5	32859911
AllCCS	[M+Na]+	173.4	32859911
AllCCS	[M-H]-	174.6	32859911
AllCCS	[M+Na-2H]-	174.1	32859911
AllCCS	[M+HCOO]-	173.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nordihydrocodeine	[H][C@@]12CC3=C4C(OC5[C@@H](O)CCC1[C@@]45CCN2)=C(OC)C=C3	3848.4	Standard polar	33892256
Nordihydrocodeine	[H][C@@]12CC3=C4C(OC5[C@@H](O)CCC1[C@@]45CCN2)=C(OC)C=C3	2360.8	Standard non polar	33892256
Nordihydrocodeine	[H][C@@]12CC3=C4C(OC5[C@@H](O)CCC1[C@@]45CCN2)=C(OC)C=C3	2525.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nordihydrocodeine,1TMS,isomer #1	COC1=CC=C2C[C@H]3NCC[C@]45C2=C1OC4[C@@H](O[Si](C)(C)C)CCC35	2462.5	Semi standard non polar	33892256
Nordihydrocodeine,1TMS,isomer #2	COC1=CC=C2C[C@@H]3C4CC[C@H](O)C5OC1=C2[C@@]54CCN3[Si](C)(C)C	2480.0	Semi standard non polar	33892256
Nordihydrocodeine,2TMS,isomer #1	COC1=CC=C2C[C@@H]3C4CC[C@H](O[Si](C)(C)C)C5OC1=C2[C@@]54CCN3[Si](C)(C)C	2463.9	Semi standard non polar	33892256
Nordihydrocodeine,2TMS,isomer #1	COC1=CC=C2C[C@@H]3C4CC[C@H](O[Si](C)(C)C)C5OC1=C2[C@@]54CCN3[Si](C)(C)C	2582.3	Standard non polar	33892256
Nordihydrocodeine,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3NCC[C@]45C2=C1OC4[C@@H](O[Si](C)(C)C(C)(C)C)CCC35	2737.0	Semi standard non polar	33892256
Nordihydrocodeine,1TBDMS,isomer #2	COC1=CC=C2C[C@@H]3C4CC[C@H](O)C5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	2707.3	Semi standard non polar	33892256
Nordihydrocodeine,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3C4CC[C@H](O[Si](C)(C)C(C)(C)C)C5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	2904.1	Semi standard non polar	33892256
Nordihydrocodeine,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3C4CC[C@H](O[Si](C)(C)C(C)(C)C)C5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	3067.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocodeine GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-3090000000-880d3501a4bd46b324a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocodeine GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9125000000-dd6137cc707621c3a990	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nordihydrocodeine 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 - Nordihydrocodeine 10V, Positive-QTOF	splash10-000i-0090000000-05b76fa8fdda643f72ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 20V, Positive-QTOF	splash10-0079-0090000000-8d8297bc57d93e71ccf1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 40V, Positive-QTOF	splash10-0fg6-3090000000-7f592c23c015c2191330	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 10V, Negative-QTOF	splash10-000i-0090000000-de1cc4626a04bd741a65	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 20V, Negative-QTOF	splash10-000i-0090000000-7bbc27adb58b72b980d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 40V, Negative-QTOF	splash10-03ml-0190000000-4fa85011843596897f92	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 10V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 20V, Negative-QTOF	splash10-000i-0090000000-32affc6af32f5da1d257	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 40V, Negative-QTOF	splash10-001i-0090000000-cd618cd0fe4548931a24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 10V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 20V, Positive-QTOF	splash10-000i-0090000000-8e23f9bfe8905382513a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nordihydrocodeine 40V, Positive-QTOF	splash10-000i-0090000000-11b9dc54e69e09d5532c	2021-09-22	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

4931996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10016922

PDB ID

Not Available

ChEBI ID

174041

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 Nordihydrocodeine (HMDB0041956)

MOL for HMDB0041956 (Nordihydrocodeine)

3D MOL for HMDB0041956 (Nordihydrocodeine)

3D SDF for HMDB0041956 (Nordihydrocodeine)

3D-SDF for HMDB0041956 (Nordihydrocodeine)

PDB for HMDB0041956 (Nordihydrocodeine)

3D PDB for HMDB0041956 (Nordihydrocodeine)

SMILES for HMDB0041956 (Nordihydrocodeine)

INCHI for HMDB0041956 (Nordihydrocodeine)

Structure for HMDB0041956 (Nordihydrocodeine)

3D Structure for HMDB0041956 (Nordihydrocodeine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra