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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (49) Show 49 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-10-16 11:18:23 UTC

Update Date

2022-03-07 02:49:24 UTC

HMDB ID

HMDB0004995

Secondary Accession Numbers

HMDB0014463
HMDB04995
HMDB14463

Metabolite Identification

Common Name

Codeine

Description

In the United States, codeine is regulated by the Controlled Substances Act. It is a Schedule II controlled substance for pain-relief products containing codeine alone. In combination with aspirin or acetaminophen (paracetamol/tylenol) it is listed as Schedule III. Codeine is also available outside the United States as an over-the-counter drug (Schedule V) in liquid cough-relief formulations. Internationally, codeine is a Schedule II drug under the Single Convention on Narcotic Drugs. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. it is a Class B Drug, except for concentrations of less than 8mg when combined with paracetamol - or 12.5mg when combined with ibuprofen - which are available in many over the counter preparations. An opioid analgesic related to morphine but with less potent analgesic properties and mild sedative effects. It also acts centrally to suppress cough. Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. In the United Kingdom, codeine is regulated by the Misuse of Drugs Act 1971; Codeine or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. It is marketed as the salts codeine sulfate and codeine phosphate. Codeine hydrochloride is more commonly marketed in contintental Europe and other regions. Codeine is an alkaloid found in opium in concentrations ranging from 0.3 to 3.0 percent. While codeine can be extracted from opium, most codeine is synthesized from morphine through the process of O-methylation. Theoretically, a dose of approximately 200 mg (oral) of codeine must be administered to give equivalent analgesia to 30 mg (oral) of morphine (Rossi, 2004). It is not used, however, in single doses of greater than 60mg (and no more than 240 mg in 24 hours) since there is a ceiling effect. [PubChem]Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0004995
     RDKit          3D
Codeine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.2862   -0.4710   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0553   -0.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.3722   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -1.4296   -1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -1.8447   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -1.2285   -0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.2151   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    0.2544    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    1.2996    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    1.8208    0.8973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1648    2.8659   -0.1437 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4338    3.3367   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    2.4422   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3560    1.4313   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.6602   -0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1189   -0.7526   -0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1309   -1.6191   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.3977    0.5937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.2457    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8017   -1.2840    1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.1474    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121    0.5651    0.6026 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5595    0.0522   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2690   -1.5403   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173   -0.3101    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857   -1.9136   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1323   -2.6605   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    2.2061    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.7515    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634    4.2847   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486    3.0318   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    1.2422   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    1.1370    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -0.6551   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.6251   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -2.6629   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309   -2.0689    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.2856    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -1.3319    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307   -2.2521    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.2689    2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    0.6274    2.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.4818    2.3363 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 22 21  1  1
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  1
 11 29  1  1
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  6
 17 35  1  0
 17 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  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>
HMDB0004995

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0004995
     RDKit          3D
Codeine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.2862   -0.4710   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0553   -0.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.3722   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -1.4296   -1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -1.8447   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -1.2285   -0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.2151   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    0.2544    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    1.2996    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    1.8208    0.8973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1648    2.8659   -0.1437 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4338    3.3367   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    2.4422   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3560    1.4313   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.6602   -0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1189   -0.7526   -0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1309   -1.6191   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.3977    0.5937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.2457    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8017   -1.2840    1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.1474    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121    0.5651    0.6026 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5595    0.0522   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2690   -1.5403   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173   -0.3101    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857   -1.9136   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1323   -2.6605   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    2.2061    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.7515    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634    4.2847   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486    3.0318   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    1.2422   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    1.1370    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -0.6551   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.6251   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -2.6629   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309   -2.0689    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.2856    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -1.3319    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307   -2.2521    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.2689    2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    0.6274    2.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.4818    2.3363 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 22 21  1  1
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  1
 11 29  1  1
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  6
 17 35  1  0
 17 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
M  END

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

COMPND    HMDB0004995
HETATM    1  C1  UNL     1       5.286  -0.471  -0.595  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.102   0.055  -0.085  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.839  -0.372  -0.387  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.634  -1.430  -1.281  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.351  -1.845  -1.572  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.253  -1.228  -0.989  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.515  -0.215  -0.135  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.753   0.254   0.203  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.569   1.300   1.103  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.234   1.821   0.897  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.165   2.866  -0.144  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.434   3.337  -0.478  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.501   2.442  -1.395  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.356   1.431  -1.499  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.685   0.660  -0.301  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.119  -0.753  -0.581  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.131  -1.619  -1.271  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.598  -1.398   0.594  1.00  0.00           N  
HETATM   19  C15 UNL     1      -4.014  -1.246   0.814  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.802  -1.284   1.758  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.877  -0.147   1.850  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.512   0.565   0.603  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.560   0.052  -1.555  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.269  -1.540  -0.818  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.117  -0.310   0.142  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.486  -1.914  -1.738  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.132  -2.660  -2.259  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.082   2.206   1.881  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.410   3.752   0.245  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.563   4.285  -0.259  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.249   3.032  -2.297  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.764   1.242  -2.497  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.528   1.137   0.250  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.012  -0.655  -1.270  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.322  -1.625  -2.389  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.263  -2.663  -0.908  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.531  -2.069   0.261  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.419  -0.286   0.463  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.187  -1.332   1.920  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.231  -2.252   1.876  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.488  -1.269   2.646  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.270   0.627   2.573  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.087  -0.482   2.336  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   17
CONECT    7    8    8   22
CONECT    8    9
CONECT    9   10
CONECT   10   11   22   28
CONECT   11   12   13   29
CONECT   12   30
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   22   33
CONECT   16   17   18   34
CONECT   17   35   36
CONECT   18   19   20
CONECT   19   37   38   39
CONECT   20   21   40   41
CONECT   21   22   42   43
END

HMDB0004995
     RDKit          3D
Codeine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.2862   -0.4710   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019    0.0553   -0.0852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.3722   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -1.4296   -1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -1.8447   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -1.2285   -0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -0.2151   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    0.2544    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    1.2996    1.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    1.8208    0.8973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1648    2.8659   -0.1437 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4338    3.3367   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    2.4422   -1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3560    1.4313   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6845    0.6602   -0.3013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1189   -0.7526   -0.5807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1309   -1.6191   -1.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5982   -1.3977    0.5937 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -1.2457    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8017   -1.2840    1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8771   -0.1474    1.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121    0.5651    0.6026 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5595    0.0522   -1.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2690   -1.5403   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1173   -0.3101    0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4857   -1.9136   -1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1323   -2.6605   -2.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823    2.2061    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    3.7515    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5634    4.2847   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2486    3.0318   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643    1.2422   -2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5278    1.1370    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -0.6551   -1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3221   -1.6251   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630   -2.6629   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5309   -2.0689    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4194   -0.2856    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1868   -1.3319    1.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307   -2.2521    1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.2689    2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    0.6274    2.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -0.4818    2.3363 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 22 21  1  1
  8  3  1  0
 22 10  1  0
 17  6  1  0
 22  7  1  0
 22 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  1
 11 29  1  1
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  1
 16 34  1  6
 17 35  1  0
 17 36  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

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	MeSH, HMDB
Isocodeine	MeSH, HMDB
N-Methylmorphine	MeSH, HMDB
Ardinex	MeSH, HMDB
N Methylmorphine	MeSH, HMDB

Chemical Formula

C₁₈H₂₁NO₃

Average Molecular Weight

299.3642

Monoisotopic Molecular Weight

299.152143543

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

76-57-3

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

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	157.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.58 g/L	Not Available
LogP	1.19	AVDEEF,A ET AL. (1996)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	168.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.58 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.181	31661259
DarkChem	[M-H]-	169.425	31661259
DeepCCS	[M-2H]-	208.351	30932474
DeepCCS	[M+Na]+	184.392	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	170.1	32859911
AllCCS	[M+NH4]+	176.4	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	177.7	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Codeine	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	3769.2	Standard polar	33892256
Codeine	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	2323.0	Standard non polar	33892256
Codeine	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])C=C[C@@H]2O	2437.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Codeine,1TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	2436.8	Semi standard non polar	33892256
Codeine,1TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	2711.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-3090000000-38668348c3e45e16a9e7	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-9135000000-5476697a08758d9606ba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01ot-3950000000-e80ecb11646b4da6aa92	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT (LTQ Orbitrap XL Thermo Scientific) 60V, Positive-QTOF	splash10-0uxr-0973000000-87d07ddd2ed24b9598d7	2015-11-06	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-d68b67071bf467a42afa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-a298cedb776a11677cf7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0459000000-1a92521b38ba51a7fa81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOF	splash10-0gc1-0940000000-68cae285315cfe9c7d0e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-QTOF , positive-QTOF	splash10-0uxs-0910000000-b0c288c76c616e1a54d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0159-0390000000-ac30542a576060b3373c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-870de7833257cd342810	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-8ece718ed46e5e439112	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0139000000-7880499a47dbd2f41229	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0uxr-0973000000-87d07ddd2ed24b9598d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-015a-0920000000-4f676c9e2b42320493af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0uxr-0910000000-e67964930533268605cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-99b083bf48ae39e3cec6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-efebfbff05a4cb72fe32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0139000000-be0f9b6eaa028b54ad6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0uxr-0973000000-89bc81638a52beefd890	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-015a-0920000000-7eccc8e19d8d88b18128	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Codeine LC-ESI-ITFT , positive-QTOF	splash10-0uxr-0910000000-5809a9ed32210bcfa231	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 10V, Positive-QTOF	splash10-0udi-0029000000-426a3155887524f062f8	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 20V, Positive-QTOF	splash10-0udi-1098000000-e16cf5105c8be7f2dd00	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 40V, Positive-QTOF	splash10-0a4i-4090000000-7d22a9e9b2e7b780b7b6	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 10V, Negative-QTOF	splash10-0002-0090000000-d34a35c4caed20d97ad0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 20V, Negative-QTOF	splash10-0002-0090000000-16ee1c88e7d182e8ebf4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine 40V, Negative-QTOF	splash10-003f-1290000000-b1e3ca03a80d7ea7edab	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Epidermis
Hair

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.006 (0.002-0.015) uM	Infant (0-1 year old)	Both	Normal	8260056	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00318

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Gates, Marshall. The conversion of codeinone to codeine. Journal of the American Chemical Society (1953), 75 4340-1.

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [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. [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. [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 ]
Skopp G, Potsch L, Moeller MR: On cosmetically treated hair--aspects and pitfalls of interpretation. Forensic Sci Int. 1997 Jan 17;84(1-3):43-52. [PubMed:9042709 ]
Piekoszewski W, Janowska E, Stanaszek R, Pach J, Winnik L, Karakiewicz B, Kozielec T: Determination of opiates in serum, saliva and hair addicted persons. Przegl Lek. 2001;58(4):287-9. [PubMed:11450354 ]
Hebden JM, Gilchrist PJ, Perkins AC, Wilson CG, Spiller RC: Stool water content and colonic drug absorption: contrasting effects of lactulose and codeine. Pharm Res. 1999 Aug;16(8):1254-9. [PubMed:10468028 ]
Huestis MA, Oyler JM, Cone EJ, Wstadik AT, Schoendorfer D, Joseph RE Jr: Sweat testing for cocaine, codeine and metabolites by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Oct 15;733(1-2):247-64. [PubMed:10572984 ]
Sindrup SH, Hofmann U, Asmussen J, Mikus G, Brosen K, Nielsen F, Ingwersen SH, Broen Christensen C: Impact of quinidine on plasma and cerebrospinal fluid concentrations of codeine and morphine after codeine intake. Eur J Clin Pharmacol. 1996;49(6):503-9. [PubMed:8706777 ]
Klein G, Barkworth MF, Birkenfeld A, Dyde CJ, Rehm KD, Toberich H, Cierpka H: [Relative bioavailability of paracetamol from tablets and suppositories as well as of paracetamol and codeine in a combination tablet]. Arzneimittelforschung. 1986 Mar;36(3):496-9. [PubMed:3518729 ]
O'Neal CL, Crouch DJ, Rollins DE, Fatah A, Cheever ML: Correlation of saliva codeine concentrations with plasma concentrations after oral codeine administration. J Anal Toxicol. 1999 Oct;23(6):452-9. [PubMed:10517550 ]
Hill V, Cairns T, Cheng CC, Schaffer M: Multiple aspects of hair analysis for opiates: methodology, clinical and workplace populations, codeine, and poppy seed ingestion. J Anal Toxicol. 2005 Oct;29(7):696-703. [PubMed:16419403 ]
Yue QY, Hasselstrom J, Svensson JO, Sawe J: Effect of codeine on oro-cecal transit time in Chinese healthy volunteers in comparison with Caucasian subjects. Eur J Clin Pharmacol. 1999 Jan;54(11):839-42. [PubMed:10027657 ]
Jonasson U, Jonasson B, Saldeen T, Thuen F: The prevalence of analgesics containing dextropropoxyphene or codeine in individuals suspected of driving under the influence of drugs. Forensic Sci Int. 2000 Aug 14;112(2-3):163-9. [PubMed:10940601 ]
Kintz P, Tracqui A, Mangin P: Analysis of opiates in fly larvae sampled on a putrefied cadaver. J Forensic Sci Soc. 1994 Apr-Jun;34(2):95-7. [PubMed:8035160 ]
Hofmann U, Seefried S, Schweizer E, Ebner T, Mikus G, Eichelbaum M: Highly sensitive gas chromatographic-tandem mass spectrometric method for the determination of morphine and codeine in serum and urine in the femtomolar range. J Chromatogr B Biomed Sci Appl. 1999 Apr 30;727(1-2):81-8. [PubMed:10360425 ]
Hepler BR, Sutheimer C, Sunshine I, Sebrosky GF: Combined enzyme immunoassay-LCEC method for the identification, confirmation, and quantitation of opiates in biological fluids. J Anal Toxicol. 1984 Mar-Apr;8(2):78-90. [PubMed:6371380 ]
Joseph RE Jr, Oyler JM, Wstadik AT, Ohuoha C, Cone EJ: Drug testing with alternative matrices I. Pharmacological effects and disposition of cocaine and codeine in plasma, sebum, and stratum corneum. J Anal Toxicol. 1998 Jan-Feb;22(1):6-17. [PubMed:9491963 ]
Pascual JA, Sanagustin J: Fully automated analytical method for codeine quantification in human plasma using on-line solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):295-302. [PubMed:10219671 ]
Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [PubMed:15102399 ]
Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [PubMed:11092114 ]
Schroeder K, Fahey T: Over-the-counter medications for acute cough in children and adults in ambulatory settings. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD001831. [PubMed:15495019 ]

Only showing the first 10 proteins. There are 49 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

7. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

Reactions

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Only showing the first 10 proteins. There are 49 proteins in total.

Show all enzymes and transporters

Showing metabocard for Codeine (HMDB0004995)

MOL for HMDB0004995 (Codeine)

3D MOL for HMDB0004995 (Codeine)

3D SDF for HMDB0004995 (Codeine)

3D-SDF for HMDB0004995 (Codeine)

PDB for HMDB0004995 (Codeine)

3D PDB for HMDB0004995 (Codeine)

SMILES for HMDB0004995 (Codeine)

INCHI for HMDB0004995 (Codeine)

Structure for HMDB0004995 (Codeine)

3D Structure for HMDB0004995 (Codeine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

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