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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014640

Secondary Accession Numbers

HMDB14640

Metabolite Identification

Common Name

Oxycodone

Description

Oxycodone is only found in individuals that have used or taken this drug. It is a semisynthetic derivative of codeine that acts as a narcotic analgesic more potent and addicting than codeine. [PubChem]Oxycodone acts as a weak agonist at mu, kappa, and delta opioid receptors within the central nervous system (CNS). Oxycodone primarily affects mu-type opioid receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, 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 such as oxycodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (kappa-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (mu and delta receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

Structure

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

497
  Mrv1652311071722162D          

 25 29  0  0  1  0            999 V2000
    1.9356   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -1.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -1.2588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.8462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -1.2588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6296   -0.8462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -1.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.4982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.4518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 18  1  0  0  0  0
  7  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 21  1  0  0  0  0
  4 23  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 24  1  6  0  0  0
  9 17  1  0  0  0  0
  9 25  1  1  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END

HMDB0014640
     RDKit          3D
Oxycodone
 44 48  0  0  0  0  0  0  0  0999 V2000
   -5.3700   -0.5956    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495    0.0509   -0.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937   -0.3233   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -1.3469    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.6966    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.0562    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -0.0785   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045    0.3259   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    1.3529   -1.5653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    1.9414   -1.2776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5067    2.8750   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181    3.4706    0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    3.1040    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435    1.7627    1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001    0.8948    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5596    1.5062   -0.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -0.4891    0.4497 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9524   -1.3655    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -1.0410   -0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -2.0966   -0.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -1.3244   -1.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.0432   -2.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3853    0.6992   -0.9232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6920   -0.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -0.4434    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -0.1646   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.8514    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -2.4877    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.4352   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    3.4943   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444    3.8516    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    1.9343    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3307    1.3339    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445    1.6149   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -0.3405    1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1779   -2.4193    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.3511    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.3074   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653   -1.7228    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -3.0198   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -1.7207   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641   -2.0289   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055   -0.2532   -2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.6115   -2.6673 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 23 22  1  6
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

497
  Mrv1652311071722162D          

 25 29  0  0  1  0            999 V2000
    1.9356   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -1.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349   -2.5175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440   -1.2588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.8462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9151   -1.2588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6296   -0.8462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861   -1.2588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6773   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6296   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    0.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -2.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861   -2.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    0.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9350   -1.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    1.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -1.4982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8196   -1.4518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 18  1  0  0  0  0
  7  2  1  1  0  0  0
  3 17  2  0  0  0  0
  4 21  1  0  0  0  0
  4 23  1  0  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 19  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 24  1  6  0  0  0
  9 17  1  0  0  0  0
  9 25  1  1  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 11 18  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014640

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1

> <INCHI_KEY>
BRUQQQPBMZOVGD-XFKAJCMBSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.3636

> <EXACT_MASS>
315.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.79396796732389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,17S)-17-hydroxy-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-trien-14-one

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
1.0348653926666662

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.167994531792818

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.56278837457051

> <JCHEM_PKA_STRONGEST_BASIC>
8.210139491712884

> <JCHEM_POLAR_SURFACE_AREA>
59.00000000000001

> <JCHEM_REFRACTIVITY>
84.04180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,13R,17S)-17-hydroxy-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-trien-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014640
     RDKit          3D
Oxycodone
 44 48  0  0  0  0  0  0  0  0999 V2000
   -5.3700   -0.5956    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495    0.0509   -0.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937   -0.3233   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -1.3469    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.6966    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.0562    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -0.0785   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045    0.3259   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    1.3529   -1.5653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    1.9414   -1.2776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5067    2.8750   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181    3.4706    0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    3.1040    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435    1.7627    1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001    0.8948    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5596    1.5062   -0.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -0.4891    0.4497 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9524   -1.3655    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -1.0410   -0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -2.0966   -0.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -1.3244   -1.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.0432   -2.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3853    0.6992   -0.9232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6920   -0.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -0.4434    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -0.1646   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.8514    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -2.4877    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.4352   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    3.4943   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444    3.8516    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    1.9343    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3307    1.3339    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445    1.6149   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -0.3405    1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1779   -2.4193    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.3511    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.3074   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653   -1.7228    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -3.0198   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -1.7207   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641   -2.0289   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055   -0.2532   -2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.6115   -2.6673 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 23 22  1  6
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 07-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 497                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-NOV-17         0                                  
HETATM    1  O   UNK     0       3.613  -0.724   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.349  -3.590   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.238  -4.699   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.238   3.080   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.975  -2.350   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.974  -1.580   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.308  -2.350   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.642  -1.580   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.641  -2.350   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.864  -0.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.974  -0.040   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.308  -3.890   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.642  -0.040   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.054  -0.450   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.308   0.730   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.974  -4.660   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.641  -3.890   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.641   0.730   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.079  -3.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.308   2.270   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.641   2.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.974   3.040   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.238   4.699   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       9.086  -2.797   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.397  -2.710   0.000  0.00  0.00           H+0
CONECT    1    9   18                                                       
CONECT    2    7                                                            
CONECT    3   17                                                            
CONECT    4   21   23                                                       
CONECT    5    8   14   19                                                  
CONECT    6    7    9   10   11                                             
CONECT    7    2    6    8   12                                             
CONECT    8    5    7   13   24                                             
CONECT    9    1    6   17   25                                             
CONECT   10    6   14                                                       
CONECT   11    6   15   18                                                  
CONECT   12    7   16                                                       
CONECT   13    8   15                                                       
CONECT   14    5   10                                                       
CONECT   15   11   13   20                                                  
CONECT   16   12   17                                                       
CONECT   17    3    9   16                                                  
CONECT   18    1   11   21                                                  
CONECT   19    5                                                            
CONECT   20   15   22                                                       
CONECT   21    4   18   22                                                  
CONECT   22   20   21                                                       
CONECT   23    4                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0014640
HETATM    1  C1  UNL     1      -5.370  -0.596   0.054  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.249   0.051  -0.490  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.994  -0.323  -0.098  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.814  -1.347   0.841  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.532  -1.697   1.213  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.425  -1.056   0.674  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.667  -0.078  -0.229  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.904   0.326  -0.645  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.690   1.353  -1.565  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.404   1.941  -1.278  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.507   2.875  -0.157  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.518   3.471   0.142  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.712   3.104   0.664  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.143   1.763   1.210  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.500   0.895   0.030  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.560   1.506  -0.637  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.987  -0.489   0.450  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.952  -1.366   1.055  1.00  0.00           C  
HETATM   19  N1  UNL     1       2.546  -1.041  -0.767  1.00  0.00           N  
HETATM   20  C15 UNL     1       3.479  -2.097  -0.550  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.536  -1.324  -1.748  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.844  -0.043  -2.138  1.00  0.00           C  
HETATM   23  C18 UNL     1       0.385   0.699  -0.923  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.301  -1.692  -0.143  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.441  -0.443   1.152  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.307  -0.165  -0.373  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.682  -1.851   1.265  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.348  -2.488   1.941  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.020   2.435  -2.173  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.497   3.494  -0.038  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.544   3.852   1.463  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.071   1.934   1.790  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.331   1.334   1.807  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.344   1.615  -0.062  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.807  -0.341   1.163  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.178  -2.419   0.744  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.053  -1.351   2.175  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.987  -2.307  -1.513  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.265  -1.723   0.136  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.035  -3.020  -0.129  1.00  0.00           H  
HETATM   41  H18 UNL     1       2.043  -1.721  -2.649  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.764  -2.029  -1.398  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.005  -0.253  -2.847  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.603   0.612  -2.667  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   18
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10
CONECT   10   11   23   29
CONECT   11   12   12   13
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   17   23
CONECT   16   34
CONECT   17   18   19   35
CONECT   18   36   37
CONECT   19   20   21
CONECT   20   38   39   40
CONECT   21   22   41   42
CONECT   22   23   43   44
END

HMDB0014640
     RDKit          3D
Oxycodone
 44 48  0  0  0  0  0  0  0  0999 V2000
   -5.3700   -0.5956    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2495    0.0509   -0.4897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937   -0.3233   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8144   -1.3469    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -1.6966    1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4249   -1.0562    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670   -0.0785   -0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9045    0.3259   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6896    1.3529   -1.5653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4035    1.9414   -1.2776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5067    2.8750   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181    3.4706    0.1415 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7121    3.1040    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1435    1.7627    1.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5001    0.8948    0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5596    1.5062   -0.6373 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -0.4891    0.4497 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9524   -1.3655    1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5457   -1.0410   -0.7671 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -2.0966   -0.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -1.3244   -1.7477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.0432   -2.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3853    0.6992   -0.9232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3013   -1.6920   -0.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4412   -0.4434    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -0.1646   -0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6822   -1.8514    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -2.4877    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0200    2.4352   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4972    3.4943   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5444    3.8516    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    1.9343    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3307    1.3339    1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445    1.6149   -0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8070   -0.3405    1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1779   -2.4193    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -1.3511    2.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -2.3074   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2653   -1.7228    0.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -3.0198   -0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0426   -1.7207   -2.6491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641   -2.0289   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0055   -0.2532   -2.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.6115   -2.6673 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  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 23 22  1  6
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-14-Hydroxydihydrocodeinone	ChEBI
4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one	ChEBI
4,5alpha-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one	ChEBI
Dihydro-14-hydroxycodeinone	ChEBI
Dihydrohydroxycodeinone	ChEBI
Dihydroxycodeinone	ChEBI
Oxicodona	ChEBI
Oxycodonum	ChEBI
4,5a-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one	Generator
4,5Α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one	Generator
Dihydrohydroxycondeinone	HMDB
Dihydrone	HMDB
PTI-821	HMDB
Dinarkon	HMDB
Oxiconum	HMDB
Oxycone	HMDB
Oxycontin	HMDB
Theocodin	HMDB
Eucodal	HMDB
Oxycodeinon	HMDB
Oxycodone hydrochloride	HMDB
Pancodine	HMDB
Purdue frederick brand OF oxycodone	HMDB

Chemical Formula

C₁₈H₂₁NO₄

Average Molecular Weight

315.3636

Monoisotopic Molecular Weight

315.147058165

IUPAC Name

(1S,5R,13R,17S)-17-hydroxy-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-trien-14-one

Traditional Name

(1S,5R,13R,17S)-17-hydroxy-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-trien-14-one

CAS Registry Number

76-42-6

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O

InChI Identifier

InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1

InChI Key

BRUQQQPBMZOVGD-XFKAJCMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isoquinolone
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Ketone
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Alcohol
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:7852 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014640)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Oxycodone Action Pathway (PathBank: SMP0000409)

Role

Industrial application

Mu-opioid receptor agonist (HMDB: HMDB0014640)
Opioid analgesic (HMDB: HMDB0014640)

Pharmaceutical industry

Antitussive (HMDB: HMDB0014640)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.59 g/L	Not Available
LogP	0.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	168.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.59 g/L	ALOGPS
logP	1.04	ALOGPS
logP	1.03	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	13.56	ChemAxon
pKa (Strongest Basic)	8.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.04 m³·mol⁻¹	ChemAxon
Polarizability	32.79 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]+	173.435	31661259
DarkChem	[M-H]-	171.61	31661259
DeepCCS	[M-2H]-	213.089	30932474
DeepCCS	[M+Na]+	189.126	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	180.4	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxycodone	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O	3869.9	Standard polar	33892256
Oxycodone	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O	2495.9	Standard non polar	33892256
Oxycodone	[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O	2659.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxycodone,1TMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(=O)CC[C@@]35O[Si](C)(C)C	2559.2	Semi standard non polar	33892256
Oxycodone,1TMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C)CC[C@@]34O)OC1=C25	2599.4	Semi standard non polar	33892256
Oxycodone,1TMS,isomer #3	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C)=CC[C@@]35O	2566.3	Semi standard non polar	33892256
Oxycodone,2TMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C)CC[C@@]34O[Si](C)(C)C)OC1=C25	2551.9	Semi standard non polar	33892256
Oxycodone,2TMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C)CC[C@@]34O[Si](C)(C)C)OC1=C25	2622.5	Standard non polar	33892256
Oxycodone,2TMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C)CC[C@@]34O[Si](C)(C)C)OC1=C25	3228.5	Standard polar	33892256
Oxycodone,2TMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C)=CC[C@@]35O[Si](C)(C)C	2553.0	Semi standard non polar	33892256
Oxycodone,2TMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C)=CC[C@@]35O[Si](C)(C)C	2586.7	Standard non polar	33892256
Oxycodone,2TMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C)=CC[C@@]35O[Si](C)(C)C	3200.4	Standard polar	33892256
Oxycodone,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(=O)CC[C@@]35O[Si](C)(C)C(C)(C)C	2811.2	Semi standard non polar	33892256
Oxycodone,1TBDMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C(C)(C)C)CC[C@@]34O)OC1=C25	2864.4	Semi standard non polar	33892256
Oxycodone,1TBDMS,isomer #3	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C(C)(C)C)=CC[C@@]35O	2821.3	Semi standard non polar	33892256
Oxycodone,2TBDMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C(C)(C)C)CC[C@@]34O[Si](C)(C)C(C)(C)C)OC1=C25	3027.7	Semi standard non polar	33892256
Oxycodone,2TBDMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C(C)(C)C)CC[C@@]34O[Si](C)(C)C(C)(C)C)OC1=C25	3085.8	Standard non polar	33892256
Oxycodone,2TBDMS,isomer #1	COC1=CC=C2C[C@H]3N(C)CC[C@]45C(=C(O[Si](C)(C)C(C)(C)C)CC[C@@]34O[Si](C)(C)C(C)(C)C)OC1=C25	3423.2	Standard polar	33892256
Oxycodone,2TBDMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C(C)(C)C)=CC[C@@]35O[Si](C)(C)C(C)(C)C	3029.4	Semi standard non polar	33892256
Oxycodone,2TBDMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C(C)(C)C)=CC[C@@]35O[Si](C)(C)C(C)(C)C	2984.2	Standard non polar	33892256
Oxycodone,2TBDMS,isomer #2	COC1=CC=C2C[C@H]3N(C)CC[C@]45C2=C1O[C@H]4C(O[Si](C)(C)C(C)(C)C)=CC[C@@]35O[Si](C)(C)C(C)(C)C	3388.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9061000000-5297e69aa2cc5152068f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9538000000-1b9bf2a9c0682b6738c4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxycodone GC-MS ("Oxycodone,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014i-6975000000-ecd49efa58246c903e23	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 - Oxycodone LC-ESI-QTOF , positive-QTOF	splash10-014i-0009000000-d55749fa4d1f47ce2244	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone LC-ESI-QTOF , positive-QTOF	splash10-00kb-0095000000-83c78e9e15857145cc78	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone LC-ESI-QTOF , positive-QTOF	splash10-0002-0090000000-ad908ecfa38c7efce138	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone LC-ESI-QTOF , positive-QTOF	splash10-0006-0390000000-88d302b8770cb7121937	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone LC-ESI-QTOF , positive-QTOF	splash10-03fu-0790000000-4af50b834ee854320001	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 10V, Positive-QTOF	splash10-014i-0009000000-60bc25dea256a8ba83bb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 30V, Positive-QTOF	splash10-0002-0090000000-fccf9384aae73d4c8009	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 50V, Positive-QTOF	splash10-03fu-0790000000-7931a551d5483e7067a3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 50V, Positive-QTOF	splash10-03fu-0690000000-3d8d447a366cdf1fdb74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 20V, Positive-QTOF	splash10-00kb-0096000000-55405b387941a889b750	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 40V, Positive-QTOF	splash10-0006-0390000000-1f6f5ca02d934d0d4537	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 35V, Positive-QTOF	splash10-0002-0093000000-a61df116baabe44f4c3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 50V, Positive-QTOF	splash10-03fu-0690000000-7dc7939fd86861c02ab4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 40V, Positive-QTOF	splash10-0006-0390000000-fff1638b31b7719ed170	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 10V, Positive-QTOF	splash10-014i-0009000000-377e0e430e1a242d1475	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 20V, Positive-QTOF	splash10-00kb-0095000000-f6e8b2a3a26565536bcb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 40V, Positive-QTOF	splash10-0006-0390000000-97492063e89cfb7228d2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 50V, Positive-QTOF	splash10-03fu-0690000000-f855a40fc07061c8e49a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oxycodone 30V, Positive-QTOF	splash10-0002-0090000000-e6d1bf0cfddfd668c1e7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 10V, Positive-QTOF	splash10-00kb-0095000000-187a15135033fe090084	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 20V, Positive-QTOF	splash10-0002-1091000000-36b41da08ca2b913a212	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 40V, Positive-QTOF	splash10-0a5c-5090000000-a251627d2dc7a2e0750c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 10V, Negative-QTOF	splash10-03di-0029000000-9ffd2b473cfe2ec06b32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 20V, Negative-QTOF	splash10-01ot-1096000000-a01cf940a0da1fca0ffd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxycodone 40V, Negative-QTOF	splash10-052g-2090000000-da3286e89dfed1ee6a32	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Oxycodone Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00497	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00497	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

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

DB00497

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447649

KEGG Compound ID

C08018

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxycodone

METLIN ID

Not Available

PubChem Compound

5284603

PDB ID

Not Available

ChEBI ID

7852

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

Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [PubMed:17525040 ]
Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [PubMed:18039433 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [PubMed:15039299 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [PubMed:15039299 ]

Enzyme Details

3. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Delta-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:: OPRD1
Uniprot ID:: P41143
Molecular weight:: 40412.3

References

Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [PubMed:17525040 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

6. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [PubMed:17525040 ]
Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [PubMed:18039433 ]
Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. doi: 10.1093/bja/aep129. Epub 2009 May 27. [PubMed:19474215 ]

Enzyme Details

7. Kappa-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:: OPRK1
Uniprot ID:: P41145
Molecular weight:: 42644.7

References

Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [PubMed:17525040 ]
Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [PubMed:18039433 ]
Nielsen CK, Ross FB, Lotfipour S, Saini KS, Edwards SR, Smith MT: Oxycodone and morphine have distinctly different pharmacological profiles: radioligand binding and behavioural studies in two rat models of neuropathic pain. Pain. 2007 Dec 5;132(3):289-300. Epub 2007 Apr 30. [PubMed:17467904 ]

Showing metabocard for Oxycodone (HMDB0014640)

MOL for HMDB0014640 (Oxycodone)

3D MOL for HMDB0014640 (Oxycodone)

3D SDF for HMDB0014640 (Oxycodone)

3D-SDF for HMDB0014640 (Oxycodone)

PDB for HMDB0014640 (Oxycodone)

3D PDB for HMDB0014640 (Oxycodone)

SMILES for HMDB0014640 (Oxycodone)

INCHI for HMDB0014640 (Oxycodone)

Structure for HMDB0014640 (Oxycodone)

3D Structure for HMDB0014640 (Oxycodone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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