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enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015036

Secondary Accession Numbers

HMDB15036

Metabolite Identification

Common Name

Remifentanil

Description

Remifentanil, also known as ultiva, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Remifentanil is a drug which is used for use during the induction and maintenance of general anesthesia. A piperidinecarboxylate ester that is methyl piperidine-4-carboxylate in which the hydrogen attached to the nitrogen is substituted by a 3-methoxy-3-oxopropyl group and the hydrogen at position 4 is substituted the nitrogen of N-propanoylaniline. Remifentanil is a very strong basic compound (based on its pKa). In humans, remifentanil is involved in remifentanil action pathway. Remifentanil is a potentially toxic compound.

Structure

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

899
  Mrv0541 02231215052D          

 27 28  0  0  0  0            999 V2000
    2.2820    1.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751    2.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282    3.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603   -3.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -3.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -0.6099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    1.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9268    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    2.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -1.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5906    3.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3394    2.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3394    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -2.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644    2.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5769    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 23  1  0  0  0  0
  2 13  2  0  0  0  0
  3 16  2  0  0  0  0
  4 21  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0015036
     RDKit          3D
Remifentanil
 55 56  0  0  0  0  0  0  0  0999 V2000
   -2.1131   -1.8161   -4.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.0227   -2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -0.9255   -1.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.6003   -1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272   -0.1867   -0.6414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017    0.5412   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570    1.2196    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.9244    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    1.9442    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.2739   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    0.5845   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9264   -0.2651    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.7781    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -1.3141    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.6204    2.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.0693    3.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199    1.0053    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.0680    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8784   -0.2073    0.3053 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.2357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    0.5249    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418    0.3554    1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -0.5612    1.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1886    1.1416    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5686    1.0157    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -1.0417   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -1.4300   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030   -1.0979   -4.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4222   -2.3630   -4.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -2.5286   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.0003   -3.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -1.5112   -2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5126    1.2626    1.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    2.4325    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.5002    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4616    1.2716   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4425    0.1009   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -1.6030    4.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659   -1.7483    3.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -0.1984    4.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.3093    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.8280   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    1.2895   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    1.9025    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -1.2990    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298    0.1185   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    1.5977    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    0.1048    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853    0.9015    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    1.8441   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7077    0.0793   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -1.9495   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039   -0.4129   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -2.1693   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484   -2.0531    0.6890 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  2  0
 13 15  1  0
 15 16  1  0
 12 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
 22 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  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
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
M  END

899
  Mrv0541 02231215052D          

 27 28  0  0  0  0            999 V2000
    2.2820    1.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751    2.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4282    3.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603   -3.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -3.0849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -0.6099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1018    1.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4038   -0.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0573    1.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -1.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9268    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585    2.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -1.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5906    3.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3394    2.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3394    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749   -2.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4473    3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644    2.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1644    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5769    1.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2603   -3.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 23  1  0  0  0  0
  2 13  2  0  0  0  0
  3 16  2  0  0  0  0
  4 21  1  0  0  0  0
  4 27  1  0  0  0  0
  5 21  2  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  2  0  0  0  0
 15 20  1  0  0  0  0
 16 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  2  0  0  0  0
 24 26  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015036

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3

> <INCHI_KEY>
ZTVQQQVZCWLTDF-UHFFFAOYSA-N

> <FORMULA>
C20H28N2O5

> <MOLECULAR_WEIGHT>
376.4467

> <EXACT_MASS>
376.199822016

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.82270201202426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.5152788399999992

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.508324300961132

> <JCHEM_POLAR_SURFACE_AREA>
76.15

> <JCHEM_REFRACTIVITY>
100.56150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
remifentanil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015036
     RDKit          3D
Remifentanil
 55 56  0  0  0  0  0  0  0  0999 V2000
   -2.1131   -1.8161   -4.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.0227   -2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -0.9255   -1.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.6003   -1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272   -0.1867   -0.6414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017    0.5412   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570    1.2196    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.9244    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    1.9442    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.2739   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    0.5845   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9264   -0.2651    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.7781    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -1.3141    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.6204    2.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.0693    3.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199    1.0053    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.0680    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8784   -0.2073    0.3053 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.2357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    0.5249    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418    0.3554    1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -0.5612    1.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1886    1.1416    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5686    1.0157    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -1.0417   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -1.4300   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030   -1.0979   -4.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4222   -2.3630   -4.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -2.5286   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.0003   -3.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -1.5112   -2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5126    1.2626    1.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    2.4325    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.5002    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4616    1.2716   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4425    0.1009   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -1.6030    4.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659   -1.7483    3.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -0.1984    4.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.3093    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.8280   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    1.2895   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    1.9025    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -1.2990    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298    0.1185   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    1.5977    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    0.1048    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853    0.9015    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    1.8441   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7077    0.0793   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -1.9495   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039   -0.4129   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -2.1693   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484   -2.0531    0.6890 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  2  0
 13 15  1  0
 15 16  1  0
 12 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
 22 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  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
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 899                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.260   2.405   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.180   4.379   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.399   5.972   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.219  -5.758   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.887  -5.758   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.887  -1.138   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.657   3.275   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.887   1.942   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.553   1.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.220   1.172   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.553  -0.368   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.220  -0.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.707   2.932   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.887  -2.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.197   3.275   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.389   4.792   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.553  -3.448   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.569   5.782   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.967   4.609   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.967   1.942   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.553  -4.988   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.302   7.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   3.395   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.507   4.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.507   1.942   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.277   3.275   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.219  -7.298   0.000  0.00  0.00           C+0
CONECT    1   13   23                                                       
CONECT    2   13                                                            
CONECT    3   16                                                            
CONECT    4   21   27                                                       
CONECT    5   21                                                            
CONECT    6   11   12   14                                                  
CONECT    7    8   15   16                                                  
CONECT    8    7    9   10   13                                             
CONECT    9    8   11                                                       
CONECT   10    8   12                                                       
CONECT   11    6    9                                                       
CONECT   12    6   10                                                       
CONECT   13    1    2    8                                                  
CONECT   14    6   17                                                       
CONECT   15    7   19   20                                                  
CONECT   16    3    7   18                                                  
CONECT   17   14   21                                                       
CONECT   18   16   22                                                       
CONECT   19   15   24                                                       
CONECT   20   15   25                                                       
CONECT   21    4    5   17                                                  
CONECT   22   18                                                            
CONECT   23    1                                                            
CONECT   24   19   26                                                       
CONECT   25   20   26                                                       
CONECT   26   24   25                                                       
CONECT   27    4                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0015036
HETATM    1  C1  UNL     1      -2.113  -1.816  -4.085  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.350  -1.023  -2.981  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.243  -0.926  -1.845  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.364  -1.600  -1.892  1.00  0.00           O  
HETATM    5  N1  UNL     1      -2.127  -0.187  -0.641  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.302   0.541  -0.234  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.357   1.220   0.947  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.515   1.924   1.338  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.626   1.944   0.526  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.602   1.274  -0.669  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.436   0.585  -1.028  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.926  -0.265   0.147  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.387  -0.778   1.518  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.498  -1.314   1.619  1.00  0.00           O  
HETATM   15  O3  UNL     1      -0.548  -0.620   2.570  1.00  0.00           O  
HETATM   16  C12 UNL     1      -0.903  -1.069   3.860  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.220   1.005   0.408  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.247   1.068   0.060  1.00  0.00           C  
HETATM   19  N2  UNL     1       1.878  -0.207   0.305  1.00  0.00           N  
HETATM   20  C15 UNL     1       3.282  -0.236   0.259  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.970   0.525   1.372  1.00  0.00           C  
HETATM   22  C17 UNL     1       5.442   0.355   1.153  1.00  0.00           C  
HETATM   23  O4  UNL     1       6.018  -0.561   1.791  1.00  0.00           O  
HETATM   24  O5  UNL     1       6.189   1.142   0.296  1.00  0.00           O  
HETATM   25  C18 UNL     1       7.569   1.016   0.058  1.00  0.00           C  
HETATM   26  C19 UNL     1       1.311  -1.042  -0.780  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.021  -1.430  -0.251  1.00  0.00           C  
HETATM   28  H1  UNL     1      -2.703  -1.098  -4.690  1.00  0.00           H  
HETATM   29  H2  UNL     1      -1.422  -2.363  -4.731  1.00  0.00           H  
HETATM   30  H3  UNL     1      -2.810  -2.529  -3.599  1.00  0.00           H  
HETATM   31  H4  UNL     1      -1.176   0.000  -3.441  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.396  -1.511  -2.920  1.00  0.00           H  
HETATM   33  H6  UNL     1      -2.513   1.263   1.595  1.00  0.00           H  
HETATM   34  H7  UNL     1      -4.472   2.433   2.291  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.515   2.500   0.855  1.00  0.00           H  
HETATM   36  H9  UNL     1      -6.462   1.272  -1.331  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.442   0.101  -1.993  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.036  -1.603   4.319  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.766  -1.748   3.857  1.00  0.00           H  
HETATM   40  H13 UNL     1      -1.128  -0.198   4.543  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.237   1.309   1.506  1.00  0.00           H  
HETATM   42  H15 UNL     1      -0.711   1.828  -0.148  1.00  0.00           H  
HETATM   43  H16 UNL     1       1.391   1.290  -1.015  1.00  0.00           H  
HETATM   44  H17 UNL     1       1.716   1.902   0.612  1.00  0.00           H  
HETATM   45  H18 UNL     1       3.611  -1.299   0.371  1.00  0.00           H  
HETATM   46  H19 UNL     1       3.730   0.118  -0.700  1.00  0.00           H  
HETATM   47  H20 UNL     1       3.702   1.598   1.374  1.00  0.00           H  
HETATM   48  H21 UNL     1       3.728   0.105   2.369  1.00  0.00           H  
HETATM   49  H22 UNL     1       8.185   0.901   0.959  1.00  0.00           H  
HETATM   50  H23 UNL     1       7.875   1.844  -0.609  1.00  0.00           H  
HETATM   51  H24 UNL     1       7.708   0.079  -0.541  1.00  0.00           H  
HETATM   52  H25 UNL     1       1.900  -1.949  -0.933  1.00  0.00           H  
HETATM   53  H26 UNL     1       1.204  -0.413  -1.668  1.00  0.00           H  
HETATM   54  H27 UNL     1      -0.575  -2.169  -0.840  1.00  0.00           H  
HETATM   55  H28 UNL     1       0.248  -2.053   0.689  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   17   27
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   38   39   40
CONECT   17   18   41   42
CONECT   18   19   43   44
CONECT   19   20   26
CONECT   20   21   45   46
CONECT   21   22   47   48
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   49   50   51
CONECT   26   27   52   53
CONECT   27   54   55
END

HMDB0015036
     RDKit          3D
Remifentanil
 55 56  0  0  0  0  0  0  0  0999 V2000
   -2.1131   -1.8161   -4.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.0227   -2.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427   -0.9255   -1.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.6003   -1.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272   -0.1867   -0.6414 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017    0.5412   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570    1.2196    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5150    1.9244    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    1.9442    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6020    1.2739   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363    0.5845   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9264   -0.2651    0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.7781    1.5180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -1.3141    1.6190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5480   -0.6204    2.5704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.0693    3.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199    1.0053    0.4083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2469    1.0680    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8784   -0.2073    0.3053 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.2357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    0.5249    1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4418    0.3554    1.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -0.5612    1.7911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1886    1.1416    0.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5686    1.0157    0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3110   -1.0417   -0.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213   -1.4300   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030   -1.0979   -4.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4222   -2.3630   -4.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -2.5286   -3.5992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1763    0.0003   -3.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3957   -1.5112   -2.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5126    1.2626    1.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4718    2.4325    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5152    2.5002    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4616    1.2716   -1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4425    0.1009   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -1.6030    4.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659   -1.7483    3.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -0.1984    4.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.3093    1.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    1.8280   -0.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3910    1.2895   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7163    1.9025    0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -1.2990    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7298    0.1185   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018    1.5977    1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    0.1048    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1853    0.9015    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8751    1.8441   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7077    0.0793   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8998   -1.9495   -0.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2039   -0.4129   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -2.1693   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484   -2.0531    0.6890 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  2  0
 13 15  1  0
 15 16  1  0
 12 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
 22 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  1  0
 11  6  1  0
 27 12  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
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 27 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ultiva	Kegg
Remifentanyl	HMDB
Remifentanil monohydrochloride	HMDB
Remifentanil hydrochloride	HMDB
3-(4-Methoxycarbonyl-4-((1-oxopropyl)phenylamino)-1-piperidine)propanoic acid methyl ester	HMDB

Chemical Formula

C₂₀H₂₈N₂O₅

Average Molecular Weight

376.4467

Monoisotopic Molecular Weight

376.199822016

IUPAC Name

methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

Traditional Name

remifentanil

CAS Registry Number

132875-61-7

SMILES

CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC

InChI Identifier

InChI=1S/C20H28N2O5/c1-4-17(23)22(16-8-6-5-7-9-16)20(19(25)27-3)11-14-21(15-12-20)13-10-18(24)26-2/h5-9H,4,10-15H2,1-3H3

InChI Key

ZTVQQQVZCWLTDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Piperidinecarboxylic acid
Anilide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Tertiary carboxylic acid amide
Methyl ester
Carboxamide group
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:8802 )
alpha-amino acid ester (CHEBI:8802 )
anilide (CHEBI:8802 )
piperidinecarboxylate ester (CHEBI:8802 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015036)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Remifentanil Action Pathway (PathBank: SMP0000416)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.59 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	190.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.59 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.52	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	7.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	76.15 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	100.56 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.654	31661259
DarkChem	[M-H]-	186.097	31661259
DeepCCS	[M+H]+	192.441	30932474
DeepCCS	[M-H]-	190.083	30932474
DeepCCS	[M-2H]-	224.054	30932474
DeepCCS	[M+Na]+	199.472	30932474
AllCCS	[M+H]+	190.3	32859911
AllCCS	[M+H-H2O]+	187.8	32859911
AllCCS	[M+NH4]+	192.7	32859911
AllCCS	[M+Na]+	193.3	32859911
AllCCS	[M-H]-	188.4	32859911
AllCCS	[M+Na-2H]-	189.1	32859911
AllCCS	[M+HCOO]-	190.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Remifentanil	CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC	3908.3	Standard polar	33892256
Remifentanil	CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC	2526.9	Standard non polar	33892256
Remifentanil	CCC(=O)N(C1=CC=CC=C1)C1(CCN(CCC(=O)OC)CC1)C(=O)OC	2661.9	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 - Remifentanil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0cdj-3596000000-8aae94fe8a68982e79c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Remifentanil 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 - Remifentanil LC-ESI-QTOF , positive-QTOF	splash10-004i-0009000000-b9035e2706d5ac9b57a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil LC-ESI-QTOF , positive-QTOF	splash10-02di-0397000000-c610a2d0adc44d55166b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil LC-ESI-QTOF , positive-QTOF	splash10-03di-0930000000-436dbd271b442dcde5bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil LC-ESI-QTOF , positive-QTOF	splash10-03e9-4900000000-79234a6e65fb22f3b487	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil LC-ESI-QTOF , positive-QTOF	splash10-01q9-9700000000-5ce11ade40e1a80e4958	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 50V, Positive-QTOF	splash10-01q9-9700000000-5ce11ade40e1a80e4958	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 20V, Positive-QTOF	splash10-02di-0397000000-c610a2d0adc44d55166b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 10V, Positive-QTOF	splash10-004i-0009000000-b9035e2706d5ac9b57a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 30V, Positive-QTOF	splash10-03di-0930000000-436dbd271b442dcde5bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 40V, Positive-QTOF	splash10-03e9-4900000000-79234a6e65fb22f3b487	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Remifentanil 20V, Positive-QTOF	splash10-02di-0397000000-edb4efa591a39769e8a7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 10V, Positive-QTOF	splash10-002b-1019000000-895cd186455eca8fbeea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 20V, Positive-QTOF	splash10-000j-6079000000-438fdbe9c2223c77db8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 40V, Positive-QTOF	splash10-0a4i-4090000000-85ac4b7ca639bae41a2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 10V, Negative-QTOF	splash10-004l-0009000000-d7edabb8bccdbfb37512	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 20V, Negative-QTOF	splash10-07g3-1139000000-25aef3cddeba2d8279a8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 40V, Negative-QTOF	splash10-0a7u-5391000000-1ecfe4cd5e7e949c2c35	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 10V, Positive-QTOF	splash10-004i-0119000000-bfa221650ef881388c5c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 20V, Positive-QTOF	splash10-0udl-3910000000-0ef79bd76c5c4b3d4532	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 40V, Positive-QTOF	splash10-02t9-1981000000-bb61c5be324241844d65	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 10V, Negative-QTOF	splash10-004l-0009000000-c51211999f5bc5653604	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 20V, Negative-QTOF	splash10-0a74-9687000000-2da80400bff88fa8c8ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Remifentanil 40V, Negative-QTOF	splash10-0btl-2190000000-6f4a85e52197f65ecdfd	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Remifentanil 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 DB00899	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00899	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00899

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54803

KEGG Compound ID

C08021

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Remifentanil

METLIN ID

Not Available

PubChem Compound

60815

PDB ID

Not Available

ChEBI ID

8802

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. 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

Stucke AG, Zuperku EJ, Sanchez A, Tonkovic-Capin M, Tonkovic-Capin V, Mustapic S, Stuth EA: Opioid receptors on bulbospinal respiratory neurons are not activated during neuronal depression by clinically relevant opioid concentrations. J Neurophysiol. 2008 Nov;100(5):2878-88. doi: 10.1152/jn.90620.2008. Epub 2008 Sep 24. [PubMed:18815346 ]
Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. [PubMed:15665994 ]
Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. [PubMed:15828941 ]
Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. [PubMed:15868528 ]
Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. [PubMed:16372825 ]
Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. [PubMed:16861092 ]

Enzyme Details

2. 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

Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [PubMed:16114980 ]
Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149 ]
Warner DS, Hindman BJ, Todd MM, Sawin PD, Kirchner J, Roland CL, Jamerson BD: Intracranial pressure and hemodynamic effects of remifentanil versus alfentanil in patients undergoing supratentorial craniotomy. Anesth Analg. 1996 Aug;83(2):348-53. [PubMed:8694317 ]
Guy J, Hindman BJ, Baker KZ, Borel CO, Maktabi M, Ostapkovich N, Kirchner J, Todd MM, Fogarty-Mack P, Yancy V, Sokoll MD, McAllister A, Roland C, Young WL, Warner DS: Comparison of remifentanil and fentanyl in patients undergoing craniotomy for supratentorial space-occupying lesions. Anesthesiology. 1997 Mar;86(3):514-24. [PubMed:9066316 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hoke JF, Cunningham F, James MK, Muir KT, Hoffman WE: Comparative pharmacokinetics and pharmacodynamics of remifentanil, its principle metabolite (GR90291) and alfentanil in dogs. J Pharmacol Exp Ther. 1997 Apr;281(1):226-32. [PubMed:9103501 ]
Patel SS, Spencer CM: Remifentanil. Drugs. 1996 Sep;52(3):417-27; discussion 428. [PubMed:8875131 ]

Enzyme Details

3. 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

Wong GT, Li R, Jiang LL, Irwin MG: Remifentanil post-conditioning attenuates cardiac ischemia-reperfusion injury via kappa or delta opioid receptor activation. Acta Anaesthesiol Scand. 2010 Apr;54(4):510-8. doi: 10.1111/j.1399-6576.2009.02145.x. Epub 2009 Oct 29. [PubMed:19878098 ]
Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678 ]

Showing metabocard for Remifentanil (HMDB0015036)

MOL for HMDB0015036 (Remifentanil)

3D MOL for HMDB0015036 (Remifentanil)

3D SDF for HMDB0015036 (Remifentanil)

3D-SDF for HMDB0015036 (Remifentanil)

PDB for HMDB0015036 (Remifentanil)

3D PDB for HMDB0015036 (Remifentanil)

SMILES for HMDB0015036 (Remifentanil)

INCHI for HMDB0015036 (Remifentanil)

Structure for HMDB0015036 (Remifentanil)

3D Structure for HMDB0015036 (Remifentanil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References