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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-21 13:10:20 UTC

Update Date

2021-09-14 15:47:07 UTC

HMDB ID

HMDB0061718

Secondary Accession Numbers

HMDB61718

Metabolite Identification

Common Name

3-Methylthiofentanyl

Description

3-Methylthiofentanyl 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. 3-Methylthiofentanyl is a very strong basic compound (based on its pKa). In humans, 3-methylthiofentanyl is involved in 3-methylthiofentanyl action pathway. A piperidine compound having a (2-thienyl)ethyl substituent at the 1-position, a methyl group at the 3-position and an N-phenylpropanamido group at the 4-position.

Structure

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

HMDB0061718
     RDKit          3D
3-Methylthiofentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -4.0062   -2.5587    2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -1.3705    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1213    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -1.8551    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156   -0.0569   -0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    0.7254   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521    1.6650    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991    2.4289   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166    2.2625   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8552    1.3141   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798    0.5228   -1.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    0.2760   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -0.8924   -1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527   -0.7844   -1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9017   -0.4539    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -0.1892   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054   -1.4132   -0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296   -0.9373   -0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5039   -0.8788    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7056   -0.4221   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8696   -0.0492   -1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302   -0.3525   -2.1480 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458    0.6360    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252    0.7247    0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    2.2007    0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0310   -2.5354    2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -3.4907    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -2.5219    2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507   -1.4854    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.4445    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597    1.8044    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1912    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    2.8726   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2509    1.1738   -3.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -0.2083   -2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.1349   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919   -1.8920   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -0.8435   -2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -0.1530   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295   -1.8164   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    0.5136   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989    0.3413    0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348   -1.8056   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1515   -2.1331    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2772   -1.2045    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5722   -0.3321    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7937    0.3446   -1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    0.4949    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8085    1.6001    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.1800    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759    2.8562    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    2.3470    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    2.5911    0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 11  6  1  0
 24 12  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

1439
  Mrv0541 02231215292D          

 25 27  0  0  1  0            999 V2000
    1.6971   -2.9440    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319   -2.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 25  1  0  0  0  0
  2 14  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
 11 12  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 19  1  0  0  0  0
 16 22  2  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 23  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061718

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3

> <INCHI_KEY>
SRARDYUHGVMEQI-UHFFFAOYSA-N

> <FORMULA>
C21H28N2OS

> <MOLECULAR_WEIGHT>
356.525

> <EXACT_MASS>
356.192234218

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.967321026331874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{3-methyl-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.207703480666667

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.070039089845496

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
104.89920000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylthiofentanyl

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061718
     RDKit          3D
3-Methylthiofentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -4.0062   -2.5587    2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -1.3705    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1213    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -1.8551    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156   -0.0569   -0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    0.7254   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521    1.6650    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991    2.4289   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166    2.2625   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8552    1.3141   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798    0.5228   -1.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    0.2760   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -0.8924   -1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527   -0.7844   -1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9017   -0.4539    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -0.1892   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054   -1.4132   -0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296   -0.9373   -0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5039   -0.8788    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7056   -0.4221   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8696   -0.0492   -1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302   -0.3525   -2.1480 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458    0.6360    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252    0.7247    0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    2.2007    0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0310   -2.5354    2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -3.4907    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5507   -1.4854    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.4445    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597    1.8044    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1912    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    2.8726   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2509    1.1738   -3.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -0.2083   -2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.1349   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919   -1.8920   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -0.8435   -2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3245    0.5136   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989    0.3413    0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348   -1.8056   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1515   -2.1331    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2772   -1.2045    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5722   -0.3321    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7937    0.3446   -1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    0.4949    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8085    1.6001    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.1800    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759    2.8562    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    2.3470    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    2.5911    0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 11  6  1  0
 24 12  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1439                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       3.168  -5.495   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.080   3.880   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -0.740   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.748   3.880   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.748   2.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   1.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.570   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   0.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   2.340   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -2.280   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   4.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   4.650   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   6.190   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -4.590   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   6.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415   3.880   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080   6.960   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   6.960   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748   4.650   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.660  -5.495   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   6.190   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.184  -6.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.644  -6.960   0.000  0.00  0.00           C+0
CONECT    1   16   25                                                       
CONECT    2   14                                                            
CONECT    3    8    9   11                                                  
CONECT    4    5   13   14                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    8   10                                                  
CONECT    7    5    9                                                       
CONECT    8    3    6                                                       
CONECT    9    3    7                                                       
CONECT   10    6                                                            
CONECT   11    3   12                                                       
CONECT   12   11   16                                                       
CONECT   13    4   17   18                                                  
CONECT   14    2    4   15                                                  
CONECT   15   14   19                                                       
CONECT   16    1   12   22                                                  
CONECT   17   13   20                                                       
CONECT   18   13   21                                                       
CONECT   19   15                                                            
CONECT   20   17   23                                                       
CONECT   21   18   23                                                       
CONECT   22   16   24                                                       
CONECT   23   20   21                                                       
CONECT   24   22   25                                                       
CONECT   25    1   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0061718
HETATM    1  C1  UNL     1      -4.006  -2.559   2.136  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.888  -1.371   1.204  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.492  -1.121   0.783  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.592  -1.855   1.218  1.00  0.00           O  
HETATM    5  N1  UNL     1      -2.216  -0.057  -0.104  1.00  0.00           N  
HETATM    6  C4  UNL     1      -3.300   0.725  -0.576  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.852   1.665   0.243  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.899   2.429  -0.179  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.417   2.263  -1.441  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.855   1.314  -2.261  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.780   0.523  -1.842  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.830   0.276  -0.510  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.233  -0.892  -1.171  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.253  -0.784  -1.205  1.00  0.00           C  
HETATM   15  N2  UNL     1       1.902  -0.454   0.003  1.00  0.00           N  
HETATM   16  C13 UNL     1       3.301  -0.189  -0.225  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.105  -1.413  -0.596  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.530  -0.937  -0.767  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.504  -0.879   0.199  1.00  0.00           C  
HETATM   20  C17 UNL     1       7.706  -0.422  -0.167  1.00  0.00           C  
HETATM   21  C18 UNL     1       7.870  -0.049  -1.474  1.00  0.00           C  
HETATM   22  S1  UNL     1       6.330  -0.352  -2.148  1.00  0.00           S  
HETATM   23  C19 UNL     1       1.346   0.636   0.735  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.125   0.725   0.723  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.515   2.201   0.923  1.00  0.00           C  
HETATM   26  H1  UNL     1      -5.031  -2.535   2.563  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.865  -3.491   1.542  1.00  0.00           H  
HETATM   28  H3  UNL     1      -3.300  -2.522   2.967  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.551  -1.485   0.340  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.228  -0.444   1.764  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.460   1.804   1.230  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.350   3.191   0.476  1.00  0.00           H  
HETATM   33  H8  UNL     1      -6.263   2.873  -1.792  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.251   1.174  -3.254  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.358  -0.208  -2.499  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.870   1.135  -1.232  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.592  -1.892  -0.840  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.561  -0.844  -2.267  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.551  -0.153  -2.075  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.630  -1.816  -1.499  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.324   0.514  -1.113  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.699   0.341   0.653  1.00  0.00           H  
HETATM   43  H18 UNL     1       3.735  -1.806  -1.556  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.151  -2.133   0.225  1.00  0.00           H  
HETATM   45  H20 UNL     1       6.277  -1.205   1.242  1.00  0.00           H  
HETATM   46  H21 UNL     1       8.572  -0.332   0.526  1.00  0.00           H  
HETATM   47  H22 UNL     1       8.794   0.345  -1.941  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.659   0.495   1.806  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.809   1.600   0.434  1.00  0.00           H  
HETATM   50  H25 UNL     1      -0.563   0.180   1.594  1.00  0.00           H  
HETATM   51  H26 UNL     1       0.376   2.856   0.984  1.00  0.00           H  
HETATM   52  H27 UNL     1      -1.087   2.347   1.851  1.00  0.00           H  
HETATM   53  H28 UNL     1      -1.091   2.591   0.033  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4    5
CONECT    5    6   12
CONECT    6    7    7   11
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   35
CONECT   12   13   24   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   23
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   19   19   22
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   22   47
CONECT   23   24   48   49
CONECT   24   25   50
CONECT   25   51   52   53
END

HMDB0061718
     RDKit          3D
3-Methylthiofentanyl
 53 55  0  0  0  0  0  0  0  0999 V2000
   -4.0062   -2.5587    2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -1.3705    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1213    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5924   -1.8551    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156   -0.0569   -0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003    0.7254   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8521    1.6650    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991    2.4289   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4166    2.2625   -1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8552    1.3141   -2.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7798    0.5228   -1.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    0.2760   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -0.8924   -1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2527   -0.7844   -1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9017   -0.4539    0.0028 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3005   -0.1892   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054   -1.4132   -0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296   -0.9373   -0.7667 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5039   -0.8788    0.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7056   -0.4221   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8696   -0.0492   -1.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3302   -0.3525   -2.1480 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458    0.6360    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1252    0.7247    0.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    2.2007    0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0310   -2.5354    2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -3.4907    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -2.5219    2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507   -1.4854    0.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2277   -0.4445    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597    1.8044    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    3.1912    0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628    2.8726   -1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2509    1.1738   -3.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3580   -0.2083   -2.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8700    1.1349   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919   -1.8920   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -0.8435   -2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5509   -0.1530   -2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6295   -1.8164   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245    0.5136   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6989    0.3413    0.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7348   -1.8056   -1.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1515   -2.1331    0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2772   -1.2045    1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5722   -0.3321    0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7937    0.3446   -1.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6591    0.4949    1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8085    1.6001    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.1800    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759    2.8562    0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0874    2.3470    1.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908    2.5911    0.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 15 23  1  0
 23 24  1  0
 24 25  1  0
 11  6  1  0
 24 12  1  0
 22 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methyl-thiofentanyl	ChEBI
N-(3-Methyl-1-(2-thienyl)ethyl-4-piperidinyl)-N-phenylpropanamide	ChEBI

Chemical Formula

C₂₁H₂₈N₂OS

Average Molecular Weight

356.525

Monoisotopic Molecular Weight

356.192234218

IUPAC Name

N-{3-methyl-1-[2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide

Traditional Name

3-methylthiofentanyl

CAS Registry Number

Not Available

SMILES

CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3

InChI Key

SRARDYUHGVMEQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:53763 )
monocarboxylic acid amide (CHEBI:53763 )
thiophenes (CHEBI:53763 )
anilide (CHEBI:53763 )

Ontology

Not Available

Exogenous (HMDB: HMDB0061718)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

3-Methylthiofentanyl Action Pathway (PathBank: SMP0000679)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	4.32	ALOGPS
logP	4.21	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.9 m³·mol⁻¹	ChemAxon
Polarizability	39.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.493	31661259
DarkChem	[M-H]-	179.066	31661259
DeepCCS	[M+H]+	180.444	30932474
DeepCCS	[M-H]-	178.086	30932474
DeepCCS	[M-2H]-	211.736	30932474
DeepCCS	[M+Na]+	186.963	30932474
AllCCS	[M+H]+	188.6	32859911
AllCCS	[M+H-H2O]+	185.8	32859911
AllCCS	[M+NH4]+	191.1	32859911
AllCCS	[M+Na]+	191.9	32859911
AllCCS	[M-H]-	186.0	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylthiofentanyl	CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1	3919.9	Standard polar	33892256
3-Methylthiofentanyl	CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1	2890.2	Standard non polar	33892256
3-Methylthiofentanyl	CCC(=O)N(C1CCN(CCC2=CC=CS2)CC1C)C1=CC=CC=C1	2842.9	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 - 3-Methylthiofentanyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-4491000000-03d6184b38c36d4525f3	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylthiofentanyl 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Positive-QTOF	splash10-0a4i-0119000000-54f9c1eb043c9933fcaf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Positive-QTOF	splash10-0bt9-6977000000-8f4697c94488f660e8f0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Positive-QTOF	splash10-08g0-5940000000-829c4b6545a49cfadff4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Negative-QTOF	splash10-0a4i-1019000000-744235df09c4260d5773	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Negative-QTOF	splash10-052b-3379000000-3e421b298cdc8fae4641	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Negative-QTOF	splash10-0a4r-9750000000-26f677e71ec303d732ae	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Negative-QTOF	splash10-0a4i-0009000000-91527def881cb6b04573	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Negative-QTOF	splash10-052b-5094000000-bdf6c050dbe99cba1d30	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Negative-QTOF	splash10-0006-8390000000-7771bf260f878cac442b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 10V, Positive-QTOF	splash10-0a4i-0009000000-64262cbdc554d9fb1dd5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 20V, Positive-QTOF	splash10-0pb9-0159000000-8664defa8fb87d2e89b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylthiofentanyl 40V, Positive-QTOF	splash10-03di-2920000000-e03d1cb110fd3818cf39	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
3-Methylthiofentanyl Action Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01439

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methylthiofentanyl

METLIN ID

Not Available

PubChem Compound

62296

PDB ID

Not Available

ChEBI ID

53763

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

Showing metabocard for 3-Methylthiofentanyl (HMDB0061718)

MOL for HMDB0061718 (3-Methylthiofentanyl)

3D MOL for HMDB0061718 (3-Methylthiofentanyl)

3D SDF for HMDB0061718 (3-Methylthiofentanyl)

3D-SDF for HMDB0061718 (3-Methylthiofentanyl)

PDB for HMDB0061718 (3-Methylthiofentanyl)

3D PDB for HMDB0061718 (3-Methylthiofentanyl)

SMILES for HMDB0061718 (3-Methylthiofentanyl)

INCHI for HMDB0061718 (3-Methylthiofentanyl)

Structure for HMDB0061718 (3-Methylthiofentanyl)

3D Structure for HMDB0061718 (3-Methylthiofentanyl)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra