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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014846

Secondary Accession Numbers

HMDB14846

Metabolite Identification

Common Name

Sufentanil

Description

Sufentanil is only found in individuals that have used or taken this drug. It is an opioid analgesic that is used as an adjunct in anesthesia, in balanced anesthesia, and as a primary anesthetic agent. [PubChem]Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Sufentanil's analgesic activity is, most likely, due to its conversion to morphine. Opioids open calcium-dependent inwardly rectifying potassium channels (OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

Structure

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

708
  Mrv0541 02231214562D          

 27 29  0  0  0  0            999 V2000
    3.2530   -3.1354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.5879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    1.7766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856    0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    3.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -3.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9981   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 27  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  0  0  0  0
  3 14  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
 18 23  2  0  0  0  0
 19 24  2  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

HMDB0014846
     RDKit          3D
Sufentanil
 57 59  0  0  0  0  0  0  0  0999 V2000
   -3.2868    2.6241   -2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    2.8242   -1.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2880    1.6323   -1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701    1.5672   -1.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6623    0.5310   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229    0.6339    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    0.0723   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.1800   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5767    0.8481    1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018    1.4150    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279    1.3091    1.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -0.5754    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.5892    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483   -2.7097    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -3.6468    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586   -0.2252    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.2376    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6442   -0.4309 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.8976   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    0.4360   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625    0.3627   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.6222    1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5218    0.4908    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1494    0.1110    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8638   -0.0517   -1.0951 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202   -1.8124   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -1.3229   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7120   -2.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    2.7020   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3275    3.4844   -3.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    3.2254   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    3.6436   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9176   -0.4600   -1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.2549   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5760    0.9527    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7322    1.9430    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.7425    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216   -1.0761    1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -1.9024   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711   -3.9589    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613   -3.2315    2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -4.5482    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938    0.4423    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -1.1938    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546    1.2605    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2284    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4771   -1.0970    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312   -1.7120   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972    1.1628    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    0.7967   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    0.9257    2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1373    0.6712    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2326   -0.0445   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -2.3817   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.4713    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -2.2681   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239   -0.7153   -1.9821 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
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 18 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  1  0
 25 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
M  END

708
  Mrv0541 02231214562D          

 27 29  0  0  0  0            999 V2000
    3.2530   -3.1354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.7766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.4911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.5879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    1.7766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856    0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    3.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -2.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    1.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -3.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1731   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9981   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 27  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  0  0  0  0
  3 14  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  1  0  0  0  0
 18 23  2  0  0  0  0
 19 24  2  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014846

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3

> <INCHI_KEY>
GGCSSNBKKAUURC-UHFFFAOYSA-N

> <FORMULA>
C22H30N2O2S

> <MOLECULAR_WEIGHT>
386.551

> <EXACT_MASS>
386.202798904

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.851807995765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.6051731266666662

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.864673025343079

> <JCHEM_POLAR_SURFACE_AREA>
32.78

> <JCHEM_REFRACTIVITY>
111.41590000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sufentanil

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014846
     RDKit          3D
Sufentanil
 57 59  0  0  0  0  0  0  0  0999 V2000
   -3.2868    2.6241   -2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    2.8242   -1.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2880    1.6323   -1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701    1.5672   -1.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6623    0.5310   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229    0.6339    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    0.0723   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.1800   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5767    0.8481    1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018    1.4150    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279    1.3091    1.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -0.5754    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.5892    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483   -2.7097    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -3.6468    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586   -0.2252    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.2376    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6442   -0.4309 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.8976   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    0.4360   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625    0.3627   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.6222    1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5218    0.4908    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1494    0.1110    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8638   -0.0517   -1.0951 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202   -1.8124   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -1.3229   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7120   -2.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    2.7020   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3275    3.4844   -3.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    3.2254   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    3.6436   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9176   -0.4600   -1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.2549   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5760    0.9527    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7322    1.9430    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.7425    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216   -1.0761    1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -1.9024   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711   -3.9589    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613   -3.2315    2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -4.5482    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938    0.4423    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -1.1938    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546    1.2605    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2284    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4771   -1.0970    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312   -1.7120   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972    1.1628    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    0.7967   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    0.9257    2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1373    0.6712    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2326   -0.0445   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -2.3817   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.4713    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -2.2681   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239   -0.7153   -1.9821 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
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 18 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  1  0
 25 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 708                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.072  -5.853   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.850   3.316   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.620   4.650   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.160  -1.097   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.930   3.316   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.160   1.983   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.826   1.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   1.213   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.826  -0.327   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494  -0.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.390   3.316   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.160  -2.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.470   3.316   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.160   4.650   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.826  -3.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.930   5.984   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.240   4.650   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.240   1.983   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.826  -4.948   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   4.650   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.160   7.318   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.780   4.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.780   1.983   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.581  -5.853   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.550   3.316   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.056  -7.318   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.596  -7.318   0.000  0.00  0.00           C+0
CONECT    1   19   27                                                       
CONECT    2   11   20                                                       
CONECT    3   14                                                            
CONECT    4    9   10   12                                                  
CONECT    5    6   13   14                                                  
CONECT    6    5    7    8   11                                             
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    4    7                                                       
CONECT   10    4    8                                                       
CONECT   11    2    6                                                       
CONECT   12    4   15                                                       
CONECT   13    5   17   18                                                  
CONECT   14    3    5   16                                                  
CONECT   15   12   19                                                       
CONECT   16   14   21                                                       
CONECT   17   13   22                                                       
CONECT   18   13   23                                                       
CONECT   19    1   15   24                                                  
CONECT   20    2                                                            
CONECT   21   16                                                            
CONECT   22   17   25                                                       
CONECT   23   18   25                                                       
CONECT   24   19   26                                                       
CONECT   25   22   23                                                       
CONECT   26   24   27                                                       
CONECT   27    1   26                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0014846
HETATM    1  C1  UNL     1      -3.287   2.624  -2.325  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.126   2.824  -1.391  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.288   1.632  -1.187  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.170   1.567  -1.761  1.00  0.00           O  
HETATM    5  N1  UNL     1      -1.662   0.531  -0.374  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.023   0.634   0.135  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.053   0.072  -0.550  1.00  0.00           C  
HETATM    8  C6  UNL     1      -5.350   0.180  -0.051  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.577   0.848   1.121  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.502   1.415   1.804  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.228   1.309   1.313  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.836  -0.575   0.009  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.812  -1.589   0.678  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.148  -2.710   1.093  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.986  -3.647   1.692  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.159  -0.225   1.083  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.466   0.238   0.594  1.00  0.00           C  
HETATM   18  N2  UNL     1       2.000  -0.644  -0.431  1.00  0.00           N  
HETATM   19  C15 UNL     1       3.403  -0.898  -0.133  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.086   0.436  -0.368  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.562   0.363  -0.076  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.181   0.622   1.120  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.522   0.491   1.162  1.00  0.00           C  
HETATM   24  C20 UNL     1       8.149   0.111   0.006  1.00  0.00           C  
HETATM   25  S1  UNL     1       6.864  -0.052  -1.095  1.00  0.00           S  
HETATM   26  C21 UNL     1       1.220  -1.812  -0.635  1.00  0.00           C  
HETATM   27  C22 UNL     1      -0.167  -1.323  -1.082  1.00  0.00           C  
HETATM   28  H1  UNL     1      -3.221   1.712  -2.941  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.234   2.702  -1.727  1.00  0.00           H  
HETATM   30  H3  UNL     1      -3.328   3.484  -3.022  1.00  0.00           H  
HETATM   31  H4  UNL     1      -2.503   3.225  -0.403  1.00  0.00           H  
HETATM   32  H5  UNL     1      -1.440   3.644  -1.770  1.00  0.00           H  
HETATM   33  H6  UNL     1      -3.918  -0.460  -1.470  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.206  -0.255  -0.569  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.576   0.953   1.538  1.00  0.00           H  
HETATM   36  H9  UNL     1      -4.732   1.943   2.741  1.00  0.00           H  
HETATM   37  H10 UNL     1      -2.403   1.743   1.839  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.422  -1.076   1.447  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.467  -1.902  -0.188  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.771  -3.959   0.942  1.00  0.00           H  
HETATM   41  H14 UNL     1      -2.461  -3.232   2.575  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.398  -4.548   1.986  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.294   0.442   1.860  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.343  -1.194   1.649  1.00  0.00           H  
HETATM   45  H18 UNL     1       1.555   1.260   0.226  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.176   0.228   1.497  1.00  0.00           H  
HETATM   47  H20 UNL     1       3.477  -1.097   0.970  1.00  0.00           H  
HETATM   48  H21 UNL     1       3.831  -1.712  -0.729  1.00  0.00           H  
HETATM   49  H22 UNL     1       3.597   1.163   0.330  1.00  0.00           H  
HETATM   50  H23 UNL     1       3.977   0.797  -1.419  1.00  0.00           H  
HETATM   51  H24 UNL     1       5.571   0.926   2.000  1.00  0.00           H  
HETATM   52  H25 UNL     1       8.137   0.671   2.079  1.00  0.00           H  
HETATM   53  H26 UNL     1       9.233  -0.044  -0.144  1.00  0.00           H  
HETATM   54  H27 UNL     1       1.638  -2.382  -1.493  1.00  0.00           H  
HETATM   55  H28 UNL     1       1.142  -2.471   0.246  1.00  0.00           H  
HETATM   56  H29 UNL     1      -0.726  -2.268  -1.356  1.00  0.00           H  
HETATM   57  H30 UNL     1       0.024  -0.715  -1.982  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   35
CONECT   10   11   11   36
CONECT   11   37
CONECT   12   13   16   27
CONECT   13   14   38   39
CONECT   14   15
CONECT   15   40   41   42
CONECT   16   17   43   44
CONECT   17   18   45   46
CONECT   18   19   26
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22   22   25
CONECT   22   23   51
CONECT   23   24   24   52
CONECT   24   25   53
CONECT   26   27   54   55
CONECT   27   56   57
END

HMDB0014846
     RDKit          3D
Sufentanil
 57 59  0  0  0  0  0  0  0  0999 V2000
   -3.2868    2.6241   -2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259    2.8242   -1.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2880    1.6323   -1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1701    1.5672   -1.7611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6623    0.5310   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0229    0.6339    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0535    0.0723   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505    0.1800   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5767    0.8481    1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018    1.4150    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2279    1.3091    1.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361   -0.5754    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -1.5892    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483   -2.7097    1.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9860   -3.6468    1.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586   -0.2252    1.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4659    0.2376    0.5937 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -0.6442   -0.4309 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029   -0.8976   -0.1330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863    0.4360   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625    0.3627   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1810    0.6222    1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5218    0.4908    1.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1494    0.1110    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8638   -0.0517   -1.0951 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2202   -1.8124   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1670   -1.3229   -1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209    1.7120   -2.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    2.7020   -1.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3275    3.4844   -3.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028    3.2254   -0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4402    3.6436   -1.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9176   -0.4600   -1.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2056   -0.2549   -0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5760    0.9527    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7322    1.9430    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031    1.7425    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216   -1.0761    1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4670   -1.9024   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711   -3.9589    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613   -3.2315    2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -4.5482    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938    0.4423    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3431   -1.1938    1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5546    1.2605    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.2284    1.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4771   -1.0970    0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312   -1.7120   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5972    1.1628    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774    0.7967   -1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5713    0.9257    2.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1373    0.6712    2.0791 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2326   -0.0445   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377   -2.3817   -1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417   -2.4713    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7258   -2.2681   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239   -0.7153   -1.9821 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
 12 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 18 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  1  0
 25 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamide	ChEBI
N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilide	ChEBI
Sufentanilum	ChEBI
Sufentanyl	ChEBI
Sufentanil citrate	HMDB
Hameln brand OF sufentanil citrate	HMDB
Sufenta	HMDB
Sulfentanil	HMDB
Taylor brand OF sufentanil citrate	HMDB
Sufentanil-hameln	HMDB
Sulfentanyl	HMDB
Curasan brand OF sufentanil citrate	HMDB
Sufentanil curasan	HMDB
Citrate, sufentanil	HMDB
Janssen brand OF sufentanil citrate	HMDB
Sufentanil-ratiopharm	HMDB
Ratiopharm brand OF sufentanil citrate	HMDB
SufentanilHameln	HMDB
Sufentanil ratiopharm	HMDB
Curasan, sufentanil	HMDB
Sufentanil hameln	HMDB
SufentanilRatiopharm	HMDB

Chemical Formula

C₂₂H₃₀N₂O₂S

Average Molecular Weight

386.551

Monoisotopic Molecular Weight

386.202798904

IUPAC Name

N-[4-(methoxymethyl)-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide

Traditional Name

sufentanil

CAS Registry Number

56030-54-7

SMILES

CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1

InChI Identifier

InChI=1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3

InChI Key

GGCSSNBKKAUURC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Aralkylamine
Piperidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Thiophene
Amino acid or derivatives
Carboxamide group
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:9316 )
thiophenes (CHEBI:9316 )
ether (CHEBI:9316 )
anilide (CHEBI:9316 )

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

Membrane (HMDB: HMDB0014846)

Source

Exogenous

Exogenous (HMDB: HMDB0014846)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Sufentanil Pathway (HMDB: HMDB0014846)
Sufentanil Action Pathway (PathBank: SMP0000417)

Role

Industrial application

Mu-opioid receptor agonist (HMDB: HMDB0014846)
Opioid analgesic (HMDB: HMDB0014846)
Intravenous anaesthetic (HMDB: HMDB0014846)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anaesthesia adjuvant (HMDB: HMDB0014846)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	97 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	191.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.61	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.78 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.42 m³·mol⁻¹	ChemAxon
Polarizability	43.85 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]+	189.318	31661259
DarkChem	[M-H]-	185.991	31661259
DeepCCS	[M+H]+	189.356	30932474
DeepCCS	[M-H]-	186.936	30932474
DeepCCS	[M-2H]-	221.291	30932474
DeepCCS	[M+Na]+	196.517	30932474
AllCCS	[M+H]+	193.5	32859911
AllCCS	[M+H-H2O]+	191.0	32859911
AllCCS	[M+NH4]+	195.8	32859911
AllCCS	[M+Na]+	196.5	32859911
AllCCS	[M-H]-	190.2	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	191.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.53 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4944 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.23 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1728.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	184.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	189.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	355.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	368.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	239.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	952.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	401.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1369.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	253.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	213.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sufentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1	4061.9	Standard polar	33892256
Sufentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1	2898.5	Standard non polar	33892256
Sufentanil	CCC(=O)N(C1=CC=CC=C1)C1(COC)CCN(CCC2=CC=CS2)CC1	2847.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Sufentanil 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 DB00708	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00708	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

DB00708

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

38043

KEGG Compound ID

C08022

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sufentanil

METLIN ID

Not Available

PubChem Compound

41693

PDB ID

Not Available

ChEBI ID

9316

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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 ]

Enzyme Details

2. 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

Freye E, Latasch L, Portoghese PS: The delta receptor is involved in sufentanil-induced respiratory depression--opioid subreceptors mediate different effects. Eur J Anaesthesiol. 1992 Nov;9(6):457-62. [PubMed:1330549 ]
Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. [PubMed:8612823 ]

Enzyme Details

3. 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

Hurle MA: Changes in the expression of G protein-coupled receptor kinases and beta-arrestin 2 in rat brain during opioid tolerance and supersensitivity. J Neurochem. 2001 Apr;77(2):486-92. [PubMed:11299311 ]
Levron JC: [Pharmacokinetics and pharmacodynamics of morphinomimetics in the central nervous system]. Agressologie. 1991;32(6-7):318-20. [PubMed:1688220 ]
Ilien B, Galzi JL, Mejean A, Goeldner M, Hirth C: A mu-opioid receptor-filter assay. Rapid estimation of binding affinity of ligands and reversibility of long-lasting ligand-receptor complexes. Biochem Pharmacol. 1988 Oct 15;37(20):3843-51. [PubMed:2847746 ]
Colpaert FC, Leysen JE, Michiels M, van den Hoogen RH: Epidural and intravenous sufentanil in the rat: analgesia, opiate receptor binding, and drug concentrations in plasma and brain. Anesthesiology. 1986 Jul;65(1):41-9. [PubMed:3014923 ]
Leysen JE, Gommeren W: In vitro binding properties of 3H-sufentanil, a superior ligand for the mu-opiate receptor. Arch Int Pharmacodyn Ther. 1982 Dec;260(2):287-9. [PubMed:6131653 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. 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

Zhu J, Xue JC, Law PY, Claude PA, Luo LY, Yin J, Chen C, Liu-Chen LY: The region in the mu opioid receptor conferring selectivity for sufentanil over the delta receptor is different from that over the kappa receptor. FEBS Lett. 1996 Apr 15;384(2):198-202. [PubMed:8612823 ]
Chang HM, Berde CB, Holz GG 4th, Steward GF, Kream RM: Sufentanil, morphine, met-enkephalin, and kappa-agonist (U-50,488H) inhibit substance P release from primary sensory neurons: a model for presynaptic spinal opioid actions. Anesthesiology. 1989 Apr;70(4):672-7. [PubMed:2467589 ]

Showing metabocard for Sufentanil (HMDB0014846)

MOL for HMDB0014846 (Sufentanil)

3D MOL for HMDB0014846 (Sufentanil)

3D SDF for HMDB0014846 (Sufentanil)

3D-SDF for HMDB0014846 (Sufentanil)

PDB for HMDB0014846 (Sufentanil)

3D PDB for HMDB0014846 (Sufentanil)

SMILES for HMDB0014846 (Sufentanil)

INCHI for HMDB0014846 (Sufentanil)

Structure for HMDB0014846 (Sufentanil)

3D Structure for HMDB0014846 (Sufentanil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

References

References

References

References