NP-MRD: Showing NP-Card for (-)-Codeine (NP0050961)

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Record Information

Version

2.0

Created at

2022-04-27 22:25:44 UTC

Updated at

2022-04-27 22:25:44 UTC

NP-MRD ID

NP0050961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Codeine

Description

Codeine, also known as methylmorphine or codicept, 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. Codeine is a very strong basic compound (based on its pKa). Within humans, codeine participates in a number of enzymatic reactions. In particular, codeine and uridine diphosphate glucuronic acid can be converted into codeine-6-glucuronide and uridine 5'-diphosphate through the action of the enzyme UDP-glucuronosyltransferase 2B7. In addition, codeine can be converted into norcodeine and formaldehyde; which is mediated by the enzyme cytochrome P450 3A4. In humans, codeine is involved in codeine metabolism pathway. Outside of the human body, Codeine has been detected, but not quantified in, several different foods, such as potato, rowanberries, adzuki beans, orange bell peppers, and green bell peppers. This could make codeine a potential biomarker for the consumption of these foods. (-)-Codeine is found in Papaver bracteatum, Papaver setigerum and Papaver somniferum . (-)-Codeine was first documented in 1995 (PMID: 8926744). Codeine is a potentially toxic compound (PMID: 10997932) (PMID: 12423011) (PMID: 10517543) (PMID: 10102911).

Structure

MOL 3D MOL SDF PDB SMILES InChI

318
  Mrv1652307191923432D          

 25 29  0  0  1  0            999 V2000
    1.9356   -0.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -0.9899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.5773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -0.9899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6296   -0.5773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -0.9899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773    0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.8149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9151   -1.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    2.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -1.5214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.2293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.1829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 16  1  0  0  0  0
 14  2  1  6  0  0  0
  3 20  1  0  0  0  0
  3 22  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  6 23  1  1  0  0  0
  7 11  1  0  0  0  0
  7 24  1  6  0  0  0
  8 14  1  0  0  0  0
  8 25  1  1  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  2  0  0  0  0
 16 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
    5.3247   -0.6010    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    0.0795    0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8690   -0.4721    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6819   -1.8029   -0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047   -2.3417   -0.4728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258   -1.5337   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5293   -0.2524    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7578    0.3133    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462    1.6618    0.7005 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997    2.0107    0.2842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1501    2.6122   -1.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4717    2.9648   -1.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3634    1.7359   -2.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    0.7264   -1.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6409    0.4613   -0.5409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1088   -0.9600   -0.3023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0564   -2.0065   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952   -0.9632    0.9634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0894   -0.3757    0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0169   -0.5256    2.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212    0.5328    1.8211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    0.7219    0.4269 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1255    0.1614   -0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528   -1.1779    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3179   -1.2932   -0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5630   -2.4108   -0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105   -3.3656   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685    2.7300    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4029    3.5973   -1.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    3.6834   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0174    1.9548   -3.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    0.1361   -2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4969    1.1170   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8770   -1.1657   -1.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1621   -2.6077   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365   -2.7664    0.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2187    0.0299   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8393   -1.2179    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3305    0.3665    1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -0.1519    2.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -1.4410    2.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3361    1.5434    2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1082    0.2925    2.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 22  1  0
 22 21  1  1
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  1  0
 22 10  1  0
 15 22  1  0
 11 10  1  0
  7  8  1  0
 17  6  1  0
 10 28  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 21 42  1  0
 21 43  1  0
 20 40  1  0
 20 41  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 16 34  1  6
 17 35  1  0
 17 36  1  0
 15 33  1  1
 14 32  1  0
 13 31  1  0
 11 29  1  1
 12 30  1  0
M  END

318
  Mrv1652307191923432D          

 25 29  0  0  1  0            999 V2000
    1.9356   -0.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.9190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -0.9899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.5773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -0.9899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6296   -0.5773    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -0.9899    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773    0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296    0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -1.8149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9151   -1.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    2.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -1.5214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.2293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.1829    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 16  1  0  0  0  0
 14  2  1  6  0  0  0
  3 20  1  0  0  0  0
  3 22  1  0  0  0  0
  4  7  1  0  0  0  0
  4 12  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  1  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  6 23  1  1  0  0  0
  7 11  1  0  0  0  0
  7 24  1  6  0  0  0
  8 14  1  0  0  0  0
  8 25  1  1  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  1  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  2  0  0  0  0
 16 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

> <INCHI_KEY>
OROGSEYTTFOCAN-DNJOTXNNSA-N

> <FORMULA>
C18H21NO3

> <MOLECULAR_WEIGHT>
299.3642

> <EXACT_MASS>
299.152143543

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.945923610648677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.3429512830000006

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.782739294723577

> <JCHEM_PKA_STRONGEST_BASIC>
9.19278496599547

> <JCHEM_POLAR_SURFACE_AREA>
41.93

> <JCHEM_REFRACTIVITY>
84.60470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 318                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  O   UNK     0       3.613  -0.222   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.238  -4.197   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.238   3.582   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.975  -1.848   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.974  -1.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.308  -1.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.642  -1.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.641  -1.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.864   0.052   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.974   0.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.642   0.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.054   0.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.308   1.232   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.641  -3.388   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.308  -3.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.641   1.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.974  -4.158   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.079  -3.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.308   2.772   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.641   2.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.974   3.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.238   5.201   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       8.141  -2.840   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       9.086  -2.295   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.397  -2.208   0.000  0.00  0.00           H+0
CONECT    1    8   16                                                       
CONECT    2   14                                                            
CONECT    3   20   22                                                       
CONECT    4    7   12   18                                                  
CONECT    5    6    8    9   10                                             
CONECT    6    5    7   15   23                                             
CONECT    7    4    6   11   24                                             
CONECT    8    1    5   14   25                                             
CONECT    9    5   12                                                       
CONECT   10    5   13   16                                                  
CONECT   11    7   13                                                       
CONECT   12    4    9                                                       
CONECT   13   10   11   19                                                  
CONECT   14    2    8   17                                                  
CONECT   15    6   17                                                       
CONECT   16    1   10   20                                                  
CONECT   17   14   15                                                       
CONECT   18    4                                                            
CONECT   19   13   21                                                       
CONECT   20    3   16   21                                                  
CONECT   21   19   20                                                       
CONECT   22    3                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(-)-Codeine	ChEBI
(1S,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,15-tetraen-14-ol	ChEBI
(5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol	ChEBI
7,8-Didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol	ChEBI
Codein	ChEBI
Codeina	ChEBI
Codeine anhydrous	ChEBI
Codicept	ChEBI
Coducept	ChEBI
L-Codeine	ChEBI
Methylmorphine	ChEBI
Morphine 3-methyl ether	ChEBI
Morphine monomethyl ether	ChEBI
Morphine-3-methyl ether	ChEBI
O(3)-Methylmorphine	ChEBI
(5a,6a)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol	Generator
(5Α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol	Generator
7,8-Didehydro-4,5a-epoxy-3-methoxy-17-methylmorphinan-6a-ol	Generator
7,8-Didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol	Generator
Norcodeine, N-methyl	HMDB
Norcodine, N-methyl	HMDB
O3-Methylmorphine	HMDB
Codeine phosphate	HMDB
Isocodeine	HMDB
N-Methylmorphine	HMDB
Ardinex	HMDB
N Methylmorphine	HMDB

Chemical Formula

C₁₈H₂₁NO₃

Average Mass

299.3642 Da

Monoisotopic Mass

299.15214 Da

IUPAC Name

(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol

Traditional Name

(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O

InChI Identifier

InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1

InChI Key

OROGSEYTTFOCAN-DNJOTXNNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Papaver bracteatum	LOTUS Database	35616633
Papaver setigerum	Plant	KNApSAcK
Papaver somniferum	Plant	KNApSAcK

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:16714 )
organic heteropentacyclic compound (CHEBI:16714 )
Isoquinoline alkaloids (C06174 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	1.2	ALOGPS
logP	1.34	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.6 m³·mol⁻¹	ChemAxon
Polarizability	31.95 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

External Links

HMDB ID

HMDB0004995

DrugBank ID

DB00318

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Codeine

METLIN ID

498

PubChem Compound

5284371

PDB ID

Not Available

ChEBI ID

16714

Good Scents ID

Not Available

References

General References

Wilkins DG, Haughey HM, Krueger GG, Rollins DE: Disposition of codeine in female human hair after multiple-dose administration. J Anal Toxicol. 1995 Oct;19(6):492-8. doi: 10.1093/jat/19.6.492. [PubMed:8926744 ]
Ammon S, von Richter O, Hofmann U, Thon KP, Eichelbaum M, Mikus G: In vitro interaction of codeine and diclofenac. Drug Metab Dispos. 2000 Oct;28(10):1149-52. [PubMed:10997932 ]
Ropero-Miller JD, Lambing MK, Winecker RE: Simultaneous quantitation of opioids in blood by GC-EI-MS analysis following deproteination, detautomerization of keto analytes, solid-phase extraction, and trimethylsilyl derivatization. J Anal Toxicol. 2002 Oct;26(7):524-8. doi: 10.1093/jat/26.7.524. [PubMed:12423011 ]
Joseph RE Jr, Hold KM, Wilkins DG, Rollins DE, Cone EJ: Drug testing with alternative matrices II. Mechanisms of cocaine and codeine deposition in hair. J Anal Toxicol. 1999 Oct;23(6):396-408. doi: 10.1093/jat/23.6.396. [PubMed:10517543 ]
Paul BD, Shimomura ET, Smith ML: A practical approach to determine cutoff concentrations for opiate testing with simultaneous detection of codeine, morphine, and 6-acetylmorphine in urine. Clin Chem. 1999 Apr;45(4):510-9. [PubMed:10102911 ]

Showing NP-Card for (-)-Codeine (NP0050961)

MOL for NP0050961 ((-)-Codeine)

3D MOL for NP0050961 ((-)-Codeine)

3D SDF for NP0050961 ((-)-Codeine)

3D-SDF for NP0050961 ((-)-Codeine)

PDB for NP0050961 ((-)-Codeine)

3D PDB for NP0050961 ((-)-Codeine)

SMILES for NP0050961 ((-)-Codeine)

INCHI for NP0050961 ((-)-Codeine)

Structure for NP0050961 ((-)-Codeine)

3D Structure for NP0050961 ((-)-Codeine)