Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014951

Secondary Accession Numbers

HMDB14951

Metabolite Identification

Common Name

Fentanyl

Description

Fentanyl, also known as duragesic or fentanilo, belongs to the class of organic compounds known as fentanyls. Fentanyls are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton. A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid. Fentanyl is a very strong basic compound (based on its pKa). In humans, fentanyl is involved in fentanyl action pathway. Fentanyl is a potentially toxic compound.

Structure

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

HMDB0014951
     RDKit          3D
Fentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -5.0405   -2.2245    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -0.8316    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.8953    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -2.0082   -0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.2807   -0.1580 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310    1.5394   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    2.3824    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    3.5948    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2129    3.9443   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    3.1107   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    1.9027   -1.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828    0.3172   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.1311    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224   -1.1666    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -1.0513   -0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -2.1591   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300   -2.0863    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5279   -0.8565    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.3085    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9083    1.4583    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0163    1.4341    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    0.2590   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403   -0.8831   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -1.0567   -1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4202   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8145   -2.8563   -0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1360   -2.1436    0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6461   -2.7387    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9710   -0.2023   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6541   -0.3654    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    2.0943    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233    4.2475    1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    4.9114   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791    3.4384   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139    1.2650   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    1.3814   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    0.7143    1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -0.5701    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537   -1.2177    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236   -2.1844    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -3.1402   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004   -2.1380   -1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -2.9508    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -2.1102    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    0.3817    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    2.3623    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6010    2.3195   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2660    0.2050   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -1.8200   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198   -2.1188   -1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161   -0.5485   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -1.2309   -1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    0.2537   -2.4139 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  0
 11  6  1  0
 25 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END

813
  Mrv0541 02231215012D          

 25 27  0  0  0  0            999 V2000
    1.6500    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 14  1  0  0  0  0
 13 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 17  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014951

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3

> <INCHI_KEY>
PJMPHNIQZUBGLI-UHFFFAOYSA-N

> <FORMULA>
C22H28N2O

> <MOLECULAR_WEIGHT>
336.4705

> <EXACT_MASS>
336.220163528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.03155001690744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.8154985483333332

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.767614789214603

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
103.48250000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fentanyl

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014951
     RDKit          3D
Fentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -5.0405   -2.2245    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -0.8316    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.8953    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -2.0082   -0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.2807   -0.1580 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310    1.5394   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    2.3824    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    3.5948    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2129    3.9443   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    3.1107   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    1.9027   -1.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828    0.3172   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.1311    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224   -1.1666    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -1.0513   -0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -2.1591   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300   -2.0863    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5279   -0.8565    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.3085    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9083    1.4583    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0163    1.4341    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    0.2590   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403   -0.8831   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -1.0567   -1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4202   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8145   -2.8563   -0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1360   -2.1436    0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6461   -2.7387    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9710   -0.2023   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6541   -0.3654    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    2.0943    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233    4.2475    1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    4.9114   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791    3.4384   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139    1.2650   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    1.3814   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    0.7143    1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -0.5701    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537   -1.2177    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236   -2.1844    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -3.1402   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004   -2.1380   -1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -2.9508    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -2.1102    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    0.3817    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    2.3623    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6010    2.3195   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2660    0.2050   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -1.8200   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198   -2.1188   -1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161   -0.5485   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -1.2309   -1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    0.2537   -2.4139 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  0
 11  6  1  0
 25 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 813                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   4.235   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748  -0.385   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748   4.235   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   6.545   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   6.545   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   7.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   7.315   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   6.545   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.748  -6.545   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -6.545   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -7.315   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2    7    8    9                                                  
CONECT    3    4   11   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    2    5                                                       
CONECT    8    2    6                                                       
CONECT    9    2   10                                                       
CONECT   10    9   13                                                       
CONECT   11    3   15   16                                                  
CONECT   12    1    3   14                                                  
CONECT   13   10   18   19                                                  
CONECT   14   12   17                                                       
CONECT   15   11   20                                                       
CONECT   16   11   21                                                       
CONECT   17   14                                                            
CONECT   18   13   23                                                       
CONECT   19   13   24                                                       
CONECT   20   15   22                                                       
CONECT   21   16   22                                                       
CONECT   22   20   21                                                       
CONECT   23   18   25                                                       
CONECT   24   19   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014951
HETATM    1  C1  UNL     1      -5.040  -2.224   0.328  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.428  -0.832   0.219  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.967  -0.895   0.010  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.409  -2.008  -0.011  1.00  0.00           O  
HETATM    5  N1  UNL     1      -2.228   0.281  -0.158  1.00  0.00           N  
HETATM    6  C4  UNL     1      -2.931   1.539  -0.176  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.740   2.382   0.914  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.392   3.595   0.955  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.213   3.944  -0.072  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.407   3.111  -1.158  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.758   1.903  -1.202  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.783   0.317  -0.293  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.140  -0.131   0.985  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.922  -1.167   0.812  1.00  0.00           C  
HETATM   15  N2  UNL     1       1.716  -1.051  -0.342  1.00  0.00           N  
HETATM   16  C13 UNL     1       2.645  -2.159  -0.413  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.730  -2.086   0.634  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.528  -0.857   0.438  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.155   0.309   1.056  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.908   1.458   0.851  1.00  0.00           C  
HETATM   21  C18 UNL     1       6.016   1.434   0.039  1.00  0.00           C  
HETATM   22  C19 UNL     1       6.400   0.259  -0.589  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.640  -0.883  -0.377  1.00  0.00           C  
HETATM   24  C21 UNL     1       0.956  -1.057  -1.533  1.00  0.00           C  
HETATM   25  C22 UNL     1      -0.386  -0.420  -1.505  1.00  0.00           C  
HETATM   26  H1  UNL     1      -4.815  -2.856  -0.525  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.136  -2.144   0.410  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.646  -2.739   1.248  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.971  -0.202  -0.498  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.654  -0.365   1.231  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.082   2.094   1.727  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.223   4.247   1.828  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.717   4.911  -0.011  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.079   3.438  -1.955  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.914   1.265  -2.052  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.503   1.381  -0.419  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.286   0.714   1.564  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.931  -0.570   1.629  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.554  -1.218   1.715  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.424  -2.184   0.769  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.106  -3.140  -0.318  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.100  -2.138  -1.421  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.401  -2.951   0.435  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.357  -2.110   1.654  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.298   0.382   1.705  1.00  0.00           H  
HETATM   46  H21 UNL     1       4.605   2.362   1.338  1.00  0.00           H  
HETATM   47  H22 UNL     1       6.601   2.319  -0.121  1.00  0.00           H  
HETATM   48  H23 UNL     1       7.266   0.205  -1.235  1.00  0.00           H  
HETATM   49  H24 UNL     1       5.916  -1.820  -0.854  1.00  0.00           H  
HETATM   50  H25 UNL     1       0.920  -2.119  -1.932  1.00  0.00           H  
HETATM   51  H26 UNL     1       1.616  -0.549  -2.313  1.00  0.00           H  
HETATM   52  H27 UNL     1      -1.128  -1.231  -1.784  1.00  0.00           H  
HETATM   53  H28 UNL     1      -0.446   0.254  -2.414  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   35
CONECT   12   13   25   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   24
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   19   19   23
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   22   47
CONECT   22   23   23   48
CONECT   23   49
CONECT   24   25   50   51
CONECT   25   52   53
END

HMDB0014951
     RDKit          3D
Fentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -5.0405   -2.2245    0.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -0.8316    0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9672   -0.8953    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085   -2.0082   -0.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2285    0.2807   -0.1580 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310    1.5394   -0.1760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397    2.3824    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3920    3.5948    0.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2129    3.9443   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4075    3.1107   -1.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7580    1.9027   -1.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7828    0.3172   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -0.1311    0.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224   -1.1666    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7161   -1.0513   -0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449   -2.1591   -0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7300   -2.0863    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5279   -0.8565    0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547    0.3085    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9083    1.4583    0.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0163    1.4341    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    0.2590   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403   -0.8831   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -1.0567   -1.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4202   -1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8145   -2.8563   -0.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1360   -2.1436    0.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6461   -2.7387    1.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9710   -0.2023   -0.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6541   -0.3654    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0820    2.0943    1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233    4.2475    1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7172    4.9114   -0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0791    3.4384   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9139    1.2650   -2.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026    1.3814   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    0.7143    1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315   -0.5701    1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5537   -1.2177    1.7153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4236   -2.1844    0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -3.1402   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1004   -2.1380   -1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4012   -2.9508    0.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571   -2.1102    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978    0.3817    1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6051    2.3623    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6010    2.3195   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2660    0.2050   -1.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9162   -1.8200   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9198   -2.1188   -1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6161   -0.5485   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -1.2309   -1.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4458    0.2537   -2.4139 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
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 15 24  1  0
 24 25  1  0
 11  6  1  0
 25 12  1  0
 23 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 22 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Phenethyl-4-(N-phenylpropionamido)piperidine	ChEBI
1-Phenethyl-4-N-propionylanilinopiperidine	ChEBI
Duragesic	ChEBI
Fentanilo	ChEBI
Fentanylum	ChEBI
N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamide	ChEBI
N-(1-Phenethyl-4-piperidyl)propionanilide	ChEBI
N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide	ChEBI
N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide	ChEBI
N-Phenethyl-4-(N-propionylanilino)piperidine	ChEBI
N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide	ChEBI
Phentanyl	ChEBI
Subsys	Kegg
Fentanila	HMDB
Fentanyl citrate	HMDB
Fentanest	HMDB
Transmucosal oral fentanyl citrate	HMDB
Durogesic	HMDB
Fentora	HMDB
Cephalon brand OF fentanyl buccal oravescent	HMDB
Janssen pharmaceutica brand OF fentanyl	HMDB
Sublimaze	HMDB

Chemical Formula

C₂₂H₂₈N₂O

Average Molecular Weight

336.4705

Monoisotopic Molecular Weight

336.220163528

IUPAC Name

N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

Traditional Name

fentanyl

CAS Registry Number

437-38-7

SMILES

CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3

InChI Key

PJMPHNIQZUBGLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fentanyls. Fentanyls are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Fentanyls

Direct Parent

Fentanyls

Alternative Parents

Substituents

Fentanyl
Phenethylamine
Anilide
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:119915 )
monocarboxylic acid amide (CHEBI:119915 )
anilide (CHEBI:119915 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0014951)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fentanyl Action Pathway (PathBank: SMP0000415)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	87.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.024 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	184.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.12	ALOGPS
logP	3.82	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.48 m³·mol⁻¹	ChemAxon
Polarizability	40.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.996	31661259
DarkChem	[M-H]-	180.114	31661259
DeepCCS	[M+H]+	178.504	30932474
DeepCCS	[M-H]-	176.146	30932474
DeepCCS	[M-2H]-	210.215	30932474
DeepCCS	[M+Na]+	185.616	30932474
AllCCS	[M+H]+	185.7	32859911
AllCCS	[M+H-H2O]+	182.9	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.2	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	186.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fentanyl	CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1	3723.1	Standard polar	33892256
Fentanyl	CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1	2822.3	Standard non polar	33892256
Fentanyl	CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1	2810.5	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 - Fentanyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5930000000-f7e6ba23728816e17e78	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fentanyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fentanyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9850000000-7ce3a6f35f5dee98185f	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 - Fentanyl LC-ESI-QTOF , positive-QTOF	splash10-000i-0009000000-62593b54c6285a566893	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QTOF , positive-QTOF	splash10-000i-0209000000-d550d803c25d31570227	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QTOF , positive-QTOF	splash10-000i-0901000000-09bd125eea134f8811a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QTOF , positive-QTOF	splash10-000i-0900000000-2c34993eade063cb426f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QTOF , positive-QTOF	splash10-001r-0900000000-beb72ea99dc9c125d29b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-000i-0009000000-bf70e4d857c26d30032f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-000i-0907000000-a9f5d0c422eff1474d38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-000i-0900000000-0c03ba9ef576114a9503	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-d2a36b402c3a7424fab6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-1900000000-e0cbdfad80c306baabc1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0a4i-2900000000-ea551550ac6cbe6d3960	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0pdi-8900000000-89b1a77e558ec74cf3ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0kdj-9400000000-358833c028a079789d0b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl LC-ESI-QFT , positive-QTOF	splash10-0ufs-9200000000-ff2c211a084a5f124781	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl 40V, Positive-QTOF	splash10-000i-0900000000-da874163fadaa39d25ad	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl 30V, Positive-QTOF	splash10-000i-0901000000-09bd125eea134f8811a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl 10V, Positive-QTOF	splash10-000i-0009000000-e126a8d88c9106409cac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl 20V, Positive-QTOF	splash10-000i-0209000000-d550d803c25d31570227	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fentanyl 50V, Positive-QTOF	splash10-001r-0900000000-2ed12cf85c72a16b8cdb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 10V, Positive-QTOF	splash10-000i-1239000000-6f316602b5d12ff1b1b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 20V, Positive-QTOF	splash10-0a4r-4942000000-703ee8a328127a82245c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 40V, Positive-QTOF	splash10-0a4i-4900000000-c38eaa80ecf3e4334782	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 10V, Negative-QTOF	splash10-000i-0009000000-303253b936dc7fea5dd0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 20V, Negative-QTOF	splash10-0550-3498000000-cbae1ca8da3e5b395fa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fentanyl 40V, Negative-QTOF	splash10-05dl-6930000000-8603b3c4374827ab0621	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fentanyl 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 DB00813	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00813	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

DB00813

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3228

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fentanyl

METLIN ID

Not Available

PubChem Compound

3345

PDB ID

Not Available

ChEBI ID

119915

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

Van Bever WF, Niemegeers CJ, Janssen PA: Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J Med Chem. 1974 Oct;17(10):1047-51. [PubMed:4420811 ]
Simpson DM, Messina J, Xie F, Hale M: Fentanyl buccal tablet for the relief of breakthrough pain in opioid-tolerant adult patients with chronic neuropathic pain: a multicenter, randomized, double-blind, placebo-controlled study. Clin Ther. 2007 Apr;29(4):588-601. [PubMed:17617282 ]
Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [PubMed:18001263 ]
Messina J, Darwish M, Fine PG: Fentanyl buccal tablet. Drugs Today (Barc). 2008 Jan;44(1):41-54. doi: 10.1358/dot.2008.44.1.1178469. [PubMed:18301803 ]

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

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 ]
Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]

Enzyme Details

2. 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

3. 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

Enzyme Details

4. 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

Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. [PubMed:15665994 ]
Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. [PubMed:15828941 ]
Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. [PubMed:15868528 ]
Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. [PubMed:16372825 ]
Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. [PubMed:16861092 ]
Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616 ]

Enzyme Details

5. 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

You HJ, Colpaert FC, Arendt-Nielsen L: The novel analgesic and high-efficacy 5-HT1A receptor agonist F 13640 inhibits nociceptive responses, wind-up, and after-discharges in spinal neurons and withdrawal reflexes. Exp Neurol. 2005 Jan;191(1):174-83. [PubMed:15589524 ]
Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [PubMed:16114980 ]
Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149 ]
Dosen-Micovic L, Ivanovic M, Micovic V: Steric interactions and the activity of fentanyl analogs at the mu-opioid receptor. Bioorg Med Chem. 2006 May 1;14(9):2887-95. Epub 2006 Jan 11. [PubMed:16376082 ]
Dardonville C, Fernandez-Fernandez C, Gibbons SL, Ryan GJ, Jagerovic N, Gabilondo AM, Meana JJ, Callado LF: Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the mu-opioid receptor and I2-imidazoline binding sites. Bioorg Med Chem. 2006 Oct 1;14(19):6570-80. Epub 2006 Jun 23. [PubMed:16797997 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616 ]

Enzyme Details

6. 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

Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wandel C, Kim R, Wood M, Wood A: Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein. Anesthesiology. 2002 Apr;96(4):913-20. [PubMed:11964599 ]

Showing metabocard for Fentanyl (HMDB0014951)

MOL for HMDB0014951 (Fentanyl)

3D MOL for HMDB0014951 (Fentanyl)

3D SDF for HMDB0014951 (Fentanyl)

3D-SDF for HMDB0014951 (Fentanyl)

PDB for HMDB0014951 (Fentanyl)

3D PDB for HMDB0014951 (Fentanyl)

SMILES for HMDB0014951 (Fentanyl)

INCHI for HMDB0014951 (Fentanyl)

Structure for HMDB0014951 (Fentanyl)

3D Structure for HMDB0014951 (Fentanyl)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

Transporters

References