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enzymes (4)transporters (1) Show 5 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

HMDB0014940

Secondary Accession Numbers

HMDB14940

Metabolite Identification

Common Name

Alfentanil

Description

Alfentanil, also known as rapifen or fanaxal, 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. Alfentanil is a drug which is used for the management of postoperative pain and the maintenance of general anesthesia. Alfentanil is a very strong basic compound (based on its pKa). In humans, alfentanil is involved in alfentanil action pathway. Alfentanil was discovered at Janssen Pharmaceutica in 1976. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear. While alfentanil tends to cause fewer cardiovascular complications than other similar drugs such as fentanyl and remifentanil, it tends to give stronger respiratory depression and so requires careful monitoring of breathing and vital signs. Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an agonist at mu opioid receptors. Alfentanil is a potentially toxic compound. Alfentanil is a restricted drug which is classified as Schedule II in the US, according to the U.S. DEA website. It is an analogue of fentanyl with around 1/4 to 1/10 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl. Almost exclusively used by anesthesia providers during portions of a case where quick, fast acting (though not long lasting) pain control is needed (i.e. during a nerve block, head pinning etc.) Alfentanil is administered by the parenteral (injected) route for fast onset of effects and precise control of dosage.

Structure

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

802
  Mrv0541 02231215012D          

 30 32  0  0  0  0            999 V2000
    2.5791    2.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    3.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    0.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    2.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -1.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7696   -2.4248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -3.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5147   -3.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    4.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -2.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047   -3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -4.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 23  1  0  0  0  0
  2 18  2  0  0  0  0
  3 27  2  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 10  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 19  1  0  0  0  0
  6 27  1  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  8 29  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 20  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 25 28  2  0  0  0  0
 26 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0014940
     RDKit          3D
Alfentanil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -4.6080   -0.9701   -3.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5748   -0.2386   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.5253   -1.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -1.2207   -1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760   -0.1884   -0.3267 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -0.5392    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -1.8430    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.2151    2.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122   -1.2550    3.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240    0.0517    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053    0.3983    1.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.3860   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943    1.6212   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.7261   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451    3.4995    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.5508    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    0.9016    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    0.0106    0.4986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0119    0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9475   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.0523    0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.9658    0.9675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2822   -1.8695    1.0222 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6467   -0.8856    0.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0077   -0.4707    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4556    0.5783    0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -0.3787   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5882   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099   -0.2742   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.7407   -0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707   -0.4065   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -1.9926   -3.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -1.0527   -3.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7975    0.8653   -3.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6091   -0.4323   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -2.6602    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776   -3.2683    2.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930   -1.5558    4.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990    0.7960    3.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    1.4472    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782    1.9904   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    1.3653   -2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    3.9123    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    4.4756   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    3.1398    1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    1.2051    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.4800    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.8270    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469    1.9910    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -0.1686    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410    1.0533    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -1.9353   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -0.5134   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -1.3641    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1927   -0.1647   -1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6353    1.2578    1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3133    1.1254    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9009    0.1045    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1599   -1.1545   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.5442   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.5225    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.1722   -1.7317 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  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 18 29  1  0
 29 30  1  0
 11  6  1  0
 30 12  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END

802
  Mrv0541 02231215012D          

 30 32  0  0  0  0            999 V2000
    2.5791    2.4872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916    3.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.1699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    0.1227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    2.4872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -1.9399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7696   -2.4248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -3.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5147   -3.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022    0.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4041    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1022   -1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2291    3.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    4.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    1.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347   -2.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042    2.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2047   -3.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5402   -4.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 23  1  0  0  0  0
  2 18  2  0  0  0  0
  3 27  2  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 10  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 19  1  0  0  0  0
  6 27  1  0  0  0  0
  7  9  2  0  0  0  0
  8  9  1  0  0  0  0
  8 27  1  0  0  0  0
  8 29  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 17 22  1  0  0  0  0
 18 20  1  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 25 28  2  0  0  0  0
 26 28  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014940

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3

> <INCHI_KEY>
IDBPHNDTYPBSNI-UHFFFAOYSA-N

> <FORMULA>
C21H32N6O3

> <MOLECULAR_WEIGHT>
416.5172

> <EXACT_MASS>
416.25358892

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.56566625658037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.8073737583333327

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.504330578677483

> <JCHEM_POLAR_SURFACE_AREA>
81.05000000000001

> <JCHEM_REFRACTIVITY>
118.59200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alfentanil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014940
     RDKit          3D
Alfentanil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -4.6080   -0.9701   -3.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5748   -0.2386   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.5253   -1.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -1.2207   -1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760   -0.1884   -0.3267 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -0.5392    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -1.8430    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.2151    2.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122   -1.2550    3.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240    0.0517    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053    0.3983    1.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.3860   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943    1.6212   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.7261   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451    3.4995    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.5508    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    0.9016    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    0.0106    0.4986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0119    0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9475   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.0523    0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.9658    0.9675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2822   -1.8695    1.0222 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6467   -0.8856    0.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0077   -0.4707    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4556    0.5783    0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -0.3787   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5882   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099   -0.2742   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.7407   -0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707   -0.4065   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -1.9926   -3.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -1.0527   -3.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7975    0.8653   -3.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6091   -0.4323   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -2.6602    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776   -3.2683    2.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930   -1.5558    4.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990    0.7960    3.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    1.4472    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782    1.9904   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    1.3653   -2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    3.9123    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    4.4756   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    3.1398    1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    1.2051    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.4800    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.8270    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469    1.9910    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -0.1686    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410    1.0533    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -1.9353   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -0.5134   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -1.3641    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1927   -0.1647   -1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6353    1.2578    1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3133    1.1254    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9009    0.1045    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1599   -1.1545   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.5442   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.5225    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.1722   -1.7317 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  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  2  0
 18 29  1  0
 29 30  1  0
 11  6  1  0
 30 12  1  0
 27 21  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 802                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.814   4.643   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.584   5.976   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -4.050   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.124   0.229   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.894   4.643   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.791  -3.621   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.037  -4.526   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.021  -5.991   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.561  -5.991   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.124   3.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.458   2.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.791   2.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.458   0.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.791   0.999   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.354   4.643   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.124  -1.311   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.434   4.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.124   5.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.791  -2.081   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.894   7.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.205   5.976   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.205   3.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.044   5.976   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.124   8.644   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.745   5.976   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.745   3.309   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.545  -4.526   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.515   4.643   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.115  -7.237   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.742  -8.644   0.000  0.00  0.00           C+0
CONECT    1   15   23                                                       
CONECT    2   18                                                            
CONECT    3   27                                                            
CONECT    4   13   14   16                                                  
CONECT    5   10   17   18                                                  
CONECT    6    7   19   27                                                  
CONECT    7    6    9                                                       
CONECT    8    9   27   29                                                  
CONECT    9    7    8                                                       
CONECT   10    5   11   12   15                                             
CONECT   11   10   13                                                       
CONECT   12   10   14                                                       
CONECT   13    4   11                                                       
CONECT   14    4   12                                                       
CONECT   15    1   10                                                       
CONECT   16    4   19                                                       
CONECT   17    5   21   22                                                  
CONECT   18    2    5   20                                                  
CONECT   19    6   16                                                       
CONECT   20   18   24                                                       
CONECT   21   17   25                                                       
CONECT   22   17   26                                                       
CONECT   23    1                                                            
CONECT   24   20                                                            
CONECT   25   21   28                                                       
CONECT   26   22   28                                                       
CONECT   27    3    6    8                                                  
CONECT   28   25   26                                                       
CONECT   29    8   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0014940
HETATM    1  C1  UNL     1      -4.608  -0.970  -3.760  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.575  -0.239  -2.881  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.804  -0.525  -1.480  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.880  -1.221  -1.250  1.00  0.00           O  
HETATM    5  N1  UNL     1      -3.076  -0.188  -0.327  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.693  -0.539   0.914  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.685  -1.843   1.331  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.296  -2.215   2.535  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.912  -1.255   3.308  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.924   0.052   2.898  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.305   0.398   1.687  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.742   0.386  -0.280  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.594   1.621  -1.055  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.300   2.726  -0.858  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.245   3.500   0.234  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.290   0.551   1.169  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.184   0.902   1.219  1.00  0.00           C  
HETATM   18  N2  UNL     1       0.979   0.011   0.499  1.00  0.00           N  
HETATM   19  C15 UNL     1       2.347   0.012   0.787  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.077  -0.948  -0.122  1.00  0.00           C  
HETATM   21  N3  UNL     1       4.492  -1.052   0.144  1.00  0.00           N  
HETATM   22  N4  UNL     1       4.986  -1.966   0.968  1.00  0.00           N  
HETATM   23  N5  UNL     1       6.282  -1.870   1.022  1.00  0.00           N  
HETATM   24  N6  UNL     1       6.647  -0.886   0.230  1.00  0.00           N  
HETATM   25  C17 UNL     1       8.008  -0.471   0.019  1.00  0.00           C  
HETATM   26  C18 UNL     1       8.456   0.578   0.990  1.00  0.00           C  
HETATM   27  C19 UNL     1       5.532  -0.379  -0.315  1.00  0.00           C  
HETATM   28  O3  UNL     1       5.458   0.588  -1.138  1.00  0.00           O  
HETATM   29  C20 UNL     1       0.610  -0.274  -0.812  1.00  0.00           C  
HETATM   30  C21 UNL     1      -0.839  -0.741  -0.795  1.00  0.00           C  
HETATM   31  H1  UNL     1      -4.671  -0.406  -4.704  1.00  0.00           H  
HETATM   32  H2  UNL     1      -4.187  -1.993  -3.986  1.00  0.00           H  
HETATM   33  H3  UNL     1      -5.578  -1.053  -3.268  1.00  0.00           H  
HETATM   34  H4  UNL     1      -3.797   0.865  -3.032  1.00  0.00           H  
HETATM   35  H5  UNL     1      -2.609  -0.432  -3.319  1.00  0.00           H  
HETATM   36  H6  UNL     1      -3.215  -2.660   0.772  1.00  0.00           H  
HETATM   37  H7  UNL     1      -4.278  -3.268   2.843  1.00  0.00           H  
HETATM   38  H8  UNL     1      -5.393  -1.556   4.249  1.00  0.00           H  
HETATM   39  H9  UNL     1      -5.399   0.796   3.492  1.00  0.00           H  
HETATM   40  H10 UNL     1      -4.366   1.447   1.430  1.00  0.00           H  
HETATM   41  H11 UNL     1      -0.478   1.990  -0.979  1.00  0.00           H  
HETATM   42  H12 UNL     1      -1.676   1.365  -2.171  1.00  0.00           H  
HETATM   43  H13 UNL     1      -1.229   3.912   0.468  1.00  0.00           H  
HETATM   44  H14 UNL     1      -2.808   4.476  -0.062  1.00  0.00           H  
HETATM   45  H15 UNL     1      -2.809   3.140   1.071  1.00  0.00           H  
HETATM   46  H16 UNL     1      -1.872   1.205   1.779  1.00  0.00           H  
HETATM   47  H17 UNL     1      -1.337  -0.480   1.634  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.464   0.827   2.313  1.00  0.00           H  
HETATM   49  H19 UNL     1       0.347   1.991   0.985  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.593  -0.169   1.861  1.00  0.00           H  
HETATM   51  H21 UNL     1       2.741   1.053   0.564  1.00  0.00           H  
HETATM   52  H22 UNL     1       2.602  -1.935  -0.032  1.00  0.00           H  
HETATM   53  H23 UNL     1       3.015  -0.513  -1.166  1.00  0.00           H  
HETATM   54  H24 UNL     1       8.663  -1.364   0.170  1.00  0.00           H  
HETATM   55  H25 UNL     1       8.193  -0.165  -1.053  1.00  0.00           H  
HETATM   56  H26 UNL     1       7.635   1.258   1.253  1.00  0.00           H  
HETATM   57  H27 UNL     1       9.313   1.125   0.505  1.00  0.00           H  
HETATM   58  H28 UNL     1       8.901   0.105   1.909  1.00  0.00           H  
HETATM   59  H29 UNL     1       1.160  -1.154  -1.233  1.00  0.00           H  
HETATM   60  H30 UNL     1       0.792   0.544  -1.544  1.00  0.00           H  
HETATM   61  H31 UNL     1      -0.873  -1.523   0.029  1.00  0.00           H  
HETATM   62  H32 UNL     1      -1.129  -1.172  -1.732  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   36
CONECT    8    9    9   37
CONECT    9   10   38
CONECT   10   11   11   39
CONECT   11   40
CONECT   12   13   16   30
CONECT   13   14   41   42
CONECT   14   15
CONECT   15   43   44   45
CONECT   16   17   46   47
CONECT   17   18   48   49
CONECT   18   19   29
CONECT   19   20   50   51
CONECT   20   21   52   53
CONECT   21   22   27
CONECT   22   23   23
CONECT   23   24
CONECT   24   25   27
CONECT   25   26   54   55
CONECT   26   56   57   58
CONECT   27   28   28
CONECT   29   30   59   60
CONECT   30   61   62
END

HMDB0014940
     RDKit          3D
Alfentanil
 62 64  0  0  0  0  0  0  0  0999 V2000
   -4.6080   -0.9701   -3.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5748   -0.2386   -2.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -0.5253   -1.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8795   -1.2207   -1.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0760   -0.1884   -0.3267 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6930   -0.5392    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6849   -1.8430    1.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2962   -2.2151    2.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9122   -1.2550    3.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9240    0.0517    2.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053    0.3983    1.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420    0.3860   -0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5943    1.6212   -1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    2.7261   -0.8582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451    3.4995    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.5508    1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838    0.9016    1.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9787    0.0106    0.4986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3472    0.0119    0.7872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9475   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.0523    0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9860   -1.9658    0.9675 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2822   -1.8695    1.0222 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6467   -0.8856    0.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0077   -0.4707    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4556    0.5783    0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -0.3787   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5882   -1.1385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6099   -0.2742   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.7407   -0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6707   -0.4065   -4.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -1.9926   -3.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -1.0527   -3.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7975    0.8653   -3.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6091   -0.4323   -3.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2152   -2.6602    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776   -3.2683    2.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3930   -1.5558    4.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3990    0.7960    3.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    1.4472    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4782    1.9904   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6761    1.3653   -2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293    3.9123    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8084    4.4756   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8086    3.1398    1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723    1.2051    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -0.4800    1.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.8270    2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3469    1.9910    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -0.1686    1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7410    1.0533    0.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6020   -1.9353   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -0.5134   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -1.3641    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1927   -0.1647   -1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6353    1.2578    1.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3133    1.1254    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9009    0.1045    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1599   -1.1545   -1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7916    0.5442   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.5225    0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -1.1722   -1.7317 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
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  5 12  1  0
 12 13  1  0
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 12 16  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
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 20 52  1  0
 20 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 29 59  1  0
 29 60  1  0
 30 61  1  0
 30 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alfentanilum	ChEBI
Alfentanyl	ChEBI
N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide	ChEBI
Rapifen	Kegg
Esteve brand OF alfentanil hydrochloride	HMDB
Fanaxal	HMDB
ICI brand OF alfentanil hydrochloride	HMDB
Janssen brand OF alfentanil hydrochloride	HMDB
Limifen	HMDB
Alfenta	HMDB
Alfentanil hydrochloride	HMDB

Chemical Formula

C₂₁H₃₂N₆O₃

Average Molecular Weight

416.5172

Monoisotopic Molecular Weight

416.25358892

IUPAC Name

N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide

Traditional Name

alfentanil

CAS Registry Number

71195-58-9

SMILES

CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O

InChI Identifier

InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:2569 )
monocarboxylic acid amide (CHEBI:2569 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014940)
Membrane (HMDB: HMDB0014940)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Alfentanil Action Pathway (PathBank: SMP0000413)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.25 g/L	Not Available
LogP	0.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	199.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.81	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	7.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.05 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.59 m³·mol⁻¹	ChemAxon
Polarizability	45.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	197.487	31661259
DarkChem	[M-H]-	195.15	31661259
DeepCCS	[M+H]+	194.504	30932474
DeepCCS	[M-H]-	191.953	30932474
DeepCCS	[M-2H]-	226.573	30932474
DeepCCS	[M+Na]+	202.865	30932474
AllCCS	[M+H]+	199.6	32859911
AllCCS	[M+H-H2O]+	197.4	32859911
AllCCS	[M+NH4]+	201.8	32859911
AllCCS	[M+Na]+	202.4	32859911
AllCCS	[M-H]-	195.1	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	197.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alfentanil	CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O	3663.6	Standard polar	33892256
Alfentanil	CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O	3239.9	Standard non polar	33892256
Alfentanil	CCN1N=NN(CCN2CCC(COC)(CC2)N(C(=O)CC)C2=CC=CC=C2)C1=O	3202.9	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 - Alfentanil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aps-5759000000-11ce8f647981a86e2993	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alfentanil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alfentanil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil LC-ESI-QTOF , positive-QTOF	splash10-014i-0000900000-a802cc961dad7c6326a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil LC-ESI-QTOF , positive-QTOF	splash10-014i-0395300000-498fafc6962b6fd82e9c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil LC-ESI-QTOF , positive-QTOF	splash10-00kb-0912000000-43c2343a5fa4997ca93a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil LC-ESI-QTOF , positive-QTOF	splash10-015a-2900000000-16b845b2c742175e38cd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil LC-ESI-QTOF , positive-QTOF	splash10-015a-7900000000-e9bd243460dd40507619	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 40V, Positive-QTOF	splash10-015a-2900000000-16b845b2c742175e38cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 50V, Positive-QTOF	splash10-015a-7900000000-e9bd243460dd40507619	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 30V, Positive-QTOF	splash10-00kb-0912000000-43c2343a5fa4997ca93a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 30V, Positive-QTOF	splash10-00kb-0912000000-b5e89d86b302adb65517	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 40V, Positive-QTOF	splash10-015a-2900000000-d76f968c16c60e097fbc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 20V, Positive-QTOF	splash10-014i-0395300000-498fafc6962b6fd82e9c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 10V, Positive-QTOF	splash10-014i-0000900000-a802cc961dad7c6326a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 50V, Positive-QTOF	splash10-015a-7900000000-7fdf62ef447e7c6e19fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 30V, Positive-QTOF	splash10-00kb-0912000000-1f6c2333f39ce390e20e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alfentanil 50V, Positive-QTOF	splash10-015a-7900000000-1c558c3f776664f15eb1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 10V, Positive-QTOF	splash10-00di-9007000000-cbc10f94b61327a4ec79	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 20V, Positive-QTOF	splash10-0006-9022000000-5dee7e8e9ca18ed6afa7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 40V, Positive-QTOF	splash10-0006-9052000000-d1f0fa6385e6848912c6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 10V, Negative-QTOF	splash10-0cdr-6509300000-1d06eb64c3c9a376ea43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 20V, Negative-QTOF	splash10-0a4i-3109000000-3960d2bbff65d1a0ecc0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 40V, Negative-QTOF	splash10-0btc-9423000000-8194ccf6d27ec2cb2870	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 10V, Positive-QTOF	splash10-014i-0000900000-1e0b9eadc3dc511d87d7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 20V, Positive-QTOF	splash10-014i-0392100000-333cd54e08c49ae75cde	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 40V, Positive-QTOF	splash10-0296-1936000000-2f1acf618b9904cbaffe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alfentanil 10V, Negative-QTOF	splash10-014i-0009300000-f5e9f9e4f40759f2ff43	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Alfentanil 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 DB00802	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00802	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

DB00802

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

46451

KEGG Compound ID

C08005

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alfentanil

METLIN ID

Not Available

PubChem Compound

51263

PDB ID

Not Available

ChEBI ID

2569

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 ]
Klees TM, Sheffels P, Dale O, Kharasch ED: Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11. Epub 2004 Nov 22. [PubMed:15557344 ]

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

Kharasch ED, Walker A, Isoherranen N, Hoffer C, Sheffels P, Thummel K, Whittington D, Ensign D: Influence of CYP3A5 genotype on the pharmacokinetics and pharmacodynamics of the cytochrome P4503A probes alfentanil and midazolam. Clin Pharmacol Ther. 2007 Oct;82(4):410-26. Epub 2007 Jun 6. [PubMed:17554244 ]
Klees TM, Sheffels P, Dale O, Kharasch ED: Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11. Epub 2004 Nov 22. [PubMed:15557344 ]
Klees TM, Sheffels P, Thummel KE, Kharasch ED: Pharmacogenetic determinants of human liver microsomal alfentanil metabolism and the role of cytochrome P450 3A5. Anesthesiology. 2005 Mar;102(3):550-6. [PubMed:15731592 ]
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. 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

Garrido M, Gubbens-Stibbe J, Tukker E, Cox E, von Frijtag J, Kunzel D, IJzerman A, Danhof M, van der Graaf PH: Pharmacokinetic-pharmacodynamic analysis of the EEG effect of alfentanil in rats following beta-funaltrexamine-induced mu-opioid receptor "knockdown" in vivo. Pharm Res. 2000 Jun;17(6):653-9. [PubMed:10955836 ]
Lotsch J, Geisslinger G: Are mu-opioid receptor polymorphisms important for clinical opioid therapy? Trends Mol Med. 2005 Feb;11(2):82-9. [PubMed:15694871 ]
Oertel BG, Schmidt R, Schneider A, Geisslinger G, Lotsch J: The mu-opioid receptor gene polymorphism 118A>G depletes alfentanil-induced analgesia and protects against respiratory depression in homozygous carriers. Pharmacogenet Genomics. 2006 Sep;16(9):625-36. [PubMed:16906017 ]
Leung A, Wallace MS, Ridgeway B, Yaksh T: Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. Pain. 2001 Mar;91(1-2):177-87. [PubMed:11240090 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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 Alfentanil (HMDB0014940)

MOL for HMDB0014940 (Alfentanil)

3D MOL for HMDB0014940 (Alfentanil)

3D SDF for HMDB0014940 (Alfentanil)

3D-SDF for HMDB0014940 (Alfentanil)

PDB for HMDB0014940 (Alfentanil)

3D PDB for HMDB0014940 (Alfentanil)

SMILES for HMDB0014940 (Alfentanil)

INCHI for HMDB0014940 (Alfentanil)

Structure for HMDB0014940 (Alfentanil)

3D Structure for HMDB0014940 (Alfentanil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References