joint research centre - policija...joint research centre the european commission's in-house...

Joint Research CentreThe European Commission's in-house science service

ADMINISTRATIVE ARRANGEMENT JRC-Nr 33619-CLEN2SAND-DG TAXUD-Nr TAXUD/2014/DE/315

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ADMINISTRATIVE ARRANGEMENT JRC-Nr 33619-CLEN2SAND-DG TAXUD-Nr TAXUD/2014/DE/315BETWEEN DG TAXATION AND CUSTOMS UNION (DG TAXUD) AND THE JOINT RESEARCH CENTRE (JRC)for fast recognition of New Psychoactive Substances (NPS) and identification of unknown chemicalsThis report was generated on 27/01/2016 based on data from the European Customs laboratories and the JointResearch Centre. This report includes sample and molecular information, spectral data and associated tables andfigures. The chemical structure(s) was/were identified by Bio-chemical interactions & metabolomics (BCIM) groupchemists on the basis of analytical data available. NMR assignments proposed below were performed by ACD labstools in agreement with the chemical structure identified by analytical experts. Reported data are related to thesample in the following table:

Eurodat number 16010001 Received on 08 January 2016PACKAGING 1 glass vial white powder (30 mg)Registration date 08 January 2016 Name of customer Service commun des laboratoires FranceCustomer's identification 2015-30772

The following structure(s) was/were identified in the sample:

O

N

N

Data of identified compound(s)Formula C24H32N2OFW 364.5237Monoisotopic Mass 364.2515Chemicalize IUPAC name N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]pentanamideInChI (v.1.04) InChI=1S/C24H32N2O/c1-2-3-14-24(27)26(22-12-8-5-9-13-22)23-16-19-25(20-17-23)18-15-21-10-6-4-7-11-21/h4-13,23

H,2-3,14-20H2,1H3InChI Key (v.1.04) VCCPXHWAJYWQMR-UHFFFAOYSA-NSMILES (v.14.01) CCCCC(=O)N(C2CCN(CCc1ccccc1)CC2)c3ccccc3

Claude Guillou, Fabiano Reniero, Hubert Chassaigne, Joana Lobo Vicente, Veronica Holland, Salvatore Tirendi,Kamil Kolar

European Commission, Joint Research CentreInstitute for Health and Consumer Protection (IHCP)via E. Fermi, 2749TP 281 I-21027 Ispra (VA) - ItalyPhone: +39 0332 785678Fax: +39 0332 [email protected]://ihcp.jrc.ec.europa.eu



of 13

Processing and interpretation based on data provided by:Service commun des laboratoires France

Title 30772File Name \\139.191.6.82\ihcp∴I01\BIO_CHEMICAL_INTERACTION_METABONOMICS\CLEN2SAND\!PROPOSED-STRUCTURE\CLEN

_NAS\16010001_2015-30772\30772.SPADate Stamp 24 Nov 2015 13:51:25 Date 24 Nov 2015 14:51:38Technique Infrared Spectral Region IRX Axis Wavenumber (cm-1) Y Axis %ReflectanceSpectrum Range 525.0251 - 3500.1670 Points Count 6172Data Spacing 0.4821

Wavenumber (cm-1)3500 3000 2500 2000 1500

%R

efle

ctan

ce

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

3052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.283052.28

3031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.073031.07

2954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.892954.89

2858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472858.472756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.742756.74

2728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.32728.3

2704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.672704.67

2678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642678.642638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.142638.14

2508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.452508.45

2459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.282459.28

2415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.42415.4

2203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272203.272185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432185.432053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332053.332032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.62032.6

1988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251988.251949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21949.21942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451942.451770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.331770.33

1747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671747.671729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.831729.83

1714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411714.411704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281704.281688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.371688.37

1643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.541643.54

1594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.361594.36

1568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.811568.81

1492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.631492.63

1464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.671464.67

1423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.691423.69

1389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.941389.94

1373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.551373.55

1343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.661343.66

1326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.791326.79

1272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.791272.79

1245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.791245.79

1201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.921201.92

1159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.011159.01

1110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.81110.8

1076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.081076.08

1044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.261044.26

1025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.941025.94

952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18952.18

921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81921.81

877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45877.45 804.17

804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17804.17

785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37785.37

750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66750.66

701701701701701701701701701701701701701701701701701701701701701701

648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45648.45

614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7614.7

594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45594.45

545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27545.27

CH3

O

N

N



of 13

Retention Time: 6.352 Ion Mode: EI+

m/z360340320300280260240220200180160140120100806040

Rel

ativ

e In

tens

ity (%

)

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

85

90

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

364.

2563

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

273.

2000

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

230.

1838

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

189.

1000

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

160.

0999

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

146.

1000

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

132.

0999

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

118.

0957

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

105.

0996

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

96.0

998

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

783

77.0

78357

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

857

.099

8

EI+

Processing and interpretation based on data provided by:Service commun des laboratoires France

Combine <852-860> Count 299 Data Source Name 2015-30772_Centroid_EI+Data Type Condensed Date 24 Nov 2015 18:54:48Date Stamp 24 Nov 15 06:42 pmFile Name 2015-30772_Centroid_EI+ Ion Mode EI+Mass Spec Model GCMS Plot Type Stick Retention Time 6.352Sample Ds CH2Cl2/MeOH : 2015-30772 Scan 858Scan Mode Centroid Spectrum Assigned 0.0% [35-503/0-100]TIC 529.31 Total Signal 7190323.5

CH3

O

N

N



of 13

Table of fragmentsNo. Fragment Structure Formula Label m/z Calc. TIC Calc.

(%)Difference

(Da)m/z Exp. RI Exp.

(%)TIC Exp.

(%)Origin

1 8-12,20-21(-H)N11

10

9

CH8

21

20

CH2+

12

C6H10N M - C18H22NO 96.081 2.604 0.019 96.100 12.837 2.604 Manual

2 12-19

CH2+

1213

14

15

1617

18

19 C8H9 M - C16H23N2O 105.070 5.012 0.030 105.100 24.260 5.012 Manual

3 4-5,7,22-27(+H) N7

C5

22

23 24

25

2627

CH2+

4

C8H8N M - C16H24NO 118.065 1.702 0.031 118.096 8.209 1.702 Manual

4 7-8,20-27

CH+

821

20 N7 22

2324

25

2627

C9H10N M - C15H22NO 132.081 2.613 0.019 132.100 12.464 2.613 Manual

5 9-19(-H)N+

11 109

1213

14

15

1617

18

19

C10H12N M - C14H20NO 146.096 13.718 0.004 146.100 64.697 13.718 Manual

6 5-8,20-27

CH+

821

20N7

5

O6

22

23 24

25

2627 C10H10NO M - C14H22N 160.076 0.819 0.024 160.100 3.854 0.819 Manual

7 5-8,11-12,20-27(+H)N11

CH+

821

20

CH2 12

N7

C5

O6

22

23 24

25

2627

C11H13N2O M - C13H19 189.102 10.133 -0.002 189.100 46.973 10.133 Manual

8 5-13,20-27

N11

10

9 8

21

20

12

13

N7

C+

5O6

22

23 24

25

2627 C14H18N2O M - C10H14 230.141 0.774 0.042 230.184 3.471 0.774 Manual

9 1-12,20-27

N11 10

98

21

20

CH2+

12

N75

O6 22

2324

25

2627

43

2

CH31

C17H25N2O M - C7H7 273.196 23.081 0.004 273.200 100.000 23.081 Manual

10 MN

+11

10

9

821

20

1213

1415

16

17 18

19

N7

5O6

22

23 24

25

2627

4

3

2

CH31

C24H32N2O M 364.251 0.012 0.005 364.256 0.047 0.012 Manual



of 13

Data from BCIM group at JRC, IHCP IspraNMR spectraAcquisition Time (sec) 2.7263 Comment 2015-30772 10 mg in 600 uL DMSO-d6 Paris 01/ 2016Date 08 Jan 2016 15:17:51 Date Stamp 08 Jan 2016

15:17:51File Name \\139.191.6.82\ihcp∴I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_6

00\16010001\1\PDATA\1\1rFrequency (MHz) 600.13 Nucleus 1H Number of Transients 128Origin spect Original Points Count 32768 Owner nmrsuPoints Count 65536 Pulse Sequence zg30 Receiver Gain 1.91SW(cyclical) (Hz) 12019.23 Solvent DMSO-d6 Spectrum Offset (Hz) 3706.0515Spectrum Type standard Sweep Width (Hz) 12019.05 Temperature (degree C) 26.998

16010001.001.001.1r.esp

Chemical Shift (ppm)10 9 8 7 6 5 4 3 2

Nor

mal

ized

Inte

nsity

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

2.93

2.03

2.01

1.96

2.03

2.02

2.03

2.08

1.98

1.97

2.66

0.98

4.86

2.01

1.02

1.97

0.95

DMSO

M14(m, 25)

M17(m, 26,24)

M13(m, 18,16)

M16(m, 12)

M12(m, 19,15,17,27,23)

M01(t, 1)

M07(m, 13)

M09(br d, 20,10)

M08(m, 20,10)

M05(t, 4)

M11(m, 8)

M02(m, 2)

M03(quin, 3)

M04(qd, 21,9)

M06(br d, 21,9)

M15(br s, 11a) M10(br s)

δH (DMSO-d6): 10.39 (1H, br s, M15), 7.49-7.54 (2H, m, M17), 7.44-7.49 (1H, m, M14), 7.31-7.36 (2H, m,M13), 7.22-7.28 (5H, m, M12), 4.69-4.77 (1H, m, M11), 4.39 (3H, br s, M10), 3.53 (2H, br d, J=11 Hz,M09), 3.16-3.21 (2H, m, M16), 3.08-3.16 (2H, m, M08), 2.96-3.03 (2H, m, M07), 1.94 (2H, br d, J=13 Hz,M06), 1.84 (2H, t, J=7 Hz, M05), 1.65 (2H, qd, J=13 and 3 Hz, M04), 1.41 (2H, quin, J=7 Hz, M03),1.08-1.17 (2H, m, M02), 0.74 (3H, t, J=7 Hz, M01)

CH3 1

2

34

ON8

910

N+

12

13

15

1617

18

19

2021

23

2425

26

27

H11a



of 13

Table of assignments and zoomed parts:

Chemical Shift (ppm)7.7 7.6 7.5 7.4 7.3 7.2 7.1

Nor

mal

ized

Inte

nsity

0

0.25

0.50

4.86

2.01

1.02

1.97

M14(m, 25)

M17(m, 26,24)M13(m, 18,16)

M12(m, 19,15,17,27,23)

No. Atom Exp. Shift(ppm)

Multiplet

1 1 0.74 M012 2 1.12 M023 3 1.41 M034 21 1.65 M045 9 1.65 M046 4 1.84 M057 21 1.94 M068 9 1.94 M069 13 3.00 M0710 20 3.12 M0811 10 3.12 M0812 12 3.18 M1613 20 3.53 M09

No. Atom Exp. Shift(ppm)

14 10 3.5315 8 4.7316 19 7.2517 15 7.2518 17 7.2519 27 7.2520 23 7.2521 18 7.3322 16 7.3323 25 7.4724 26 7.5125 24 7.5126 11a 10.39

Chemical Shift (ppm)4.5 4.0 3.5 3.0 2.5 2.0 1.5

Nor

mal

ized

Inte

nsity

0

0.1

0.2

0.3

0.4

0.5

2.93

2.03

2.01

1.96

2.03

2.02

2.03

2.08

1.98

1.97

2.66

0.98

DMSOM16(m, 12)

M01(t, 1)

M07(m, 13)M09(br d, 20,10)

M08(m, 20,10)

M05(t, 4)

M11(m, 8)

M02(m, 2)

M03(quin, 3)

M04(qd, 21,9)

M06(br d, 21,9)

M10(br s)

CH3 1

2

34

ON8

910

N+

12

13

15

1617

18

19

2021

23

2425

26

27

H11a



of 13

16010001.002.001.1r.esp

Chemical Shift (ppm)170 160 150 140 130 120 110 100 90 80 70 60 50 40

Nor

mal

ized

Inte

nsity

-1.0

-0.9

-0.8

-0.7

-0.6

-0.5

-0.4

-0.3

-0.2

-0.1

0

0.1

0.2

0.3

0.4

0.5

0.6

DMSO

M01(s, 1)

M02(s, 2)

M03(s, 3)

M04(s, 21,9)

M05(s, 13)

M11(s, 8)

M12(s, 20,10)

M15(s, 25)

M16(s, 17)

M17(s, 18,16)

M18(s, 26,24)

M19(s, 27,23)

M20(s, 14)M21(s, 22)

M22(s, 5)M06(s, 4)

M13(s, 12)

Acquisition Time (sec) 0.9044 Comment 5 mm CPQCI 1H/19F-13C/15N/D Z-GRD Z114073/0012Date 08 Jan 2016 15:30:45 Date Stamp 08 Jan 2016 15:30:45File Name \\139.191.6.82\ihcp∴I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_6

00\16010001_2015-30772\2\PDATA\1\1rFrequency (MHz) 150.90 Nucleus 13CNumber of Transients 256 Origin spectOriginal Points Count 32768 Owner nmrsuPoints Count 32768 Pulse Sequence jmodReceiver Gain 183.05 SW(cyclical) (Hz) 36231.88Solvent DMSO-d6 Spectrum Offset (Hz) 18108.3359Spectrum Type APT Sweep Width (Hz) 36230.78Temperature (degree C) 27.002

δC (DMSO-d6): 171.9 (C-5), 138.7 (C-22), 137.6 (C-14), 130.8 (C-23, 27), 129.9 (C-24, 26), 129.1 (C-16,18), 129.1 (C-17), 129.0 (C-25), 127.2 (C-15, 19), 56.9 (C-12), 51.4 (C-10, 20), 49.5 (C-8), 34.3 (C-4),29.9 (C-13), 27.8 (C-9, 21), 27.4 (C-3), 22.1 (C-2), 14.1 (C-1)

CH3 1

2

34

5ON

89

10

N+

12

13

14

15

1617

18

19

2021

2223

2425

26

27

H



of 13

Zoomed parts:

Chemical Shift (ppm)141 140 139 138 137 136 135 134 133 132 131 130 129

Nor

mal

ized

Inte

nsity

-0.2

-0.1

0

0.1

0.2

0.3

0.4

0.5

0.6

M14(s, 19,15)M15(s, 25)

M20(s, 14)M21(s, 22)

M16(s, 17)

M17(s, 18,16)

M18(s, 26,24)

M19(s, 27,23)

CH3 1

2

34

5ON

89

10

N+

12

13

14

15

1617

18

19

2021

2223

2425

26

27

H

Chemical Shift (ppm)60 55 50 45 40 35 30 25 20

Nor

mal

ized

Inte

nsity

-0.45

-0.40

-0.35

-0.30

-0.25

-0.20

-0.15

-0.10

-0.05

0

DMSO

M11(s, 8)M01(s, 1)

M02(s, 2)

M03(s, 3)

M04(s, 21,9)

M05(s, 13)

M12(s, 20,10)

M06(s, 4)

M13(s, 12)



of 13

MS spectraCombine <2-54> Count 351Data Source Name 16010001_2015-30772_MS_50-400_1_Centroided Mass Spectrum_ES+Data Type Centroided Mass Spectrum Date 19 Jan 2016 17:26:39Date Stamp 19 Jan 2016 16:45:45 Estimated Molecular Ion 365.198File Name \\139.191.6.82\ihcp∴I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_

QTOF\16010001_2015-30772\16010001_2015-30772_MS_50-400.CDFInlet Model Electrospray Inlet Ion Mode ES+Plot Type Stick Retention Time 0.405Scan 22 Separation Type No ChromatographySpectrum Assigned 27.5% [50-400/0-100] TIC 479.63Total Signal 11909.3965

CH3

O

N

N

Retention Time: 0.405 Ion Mode: ES+

m/z3603403203002802602402202001801601401201008060

Rel

ativ

e In

tens

ity (%

)

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

85

90

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

60.0

274

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

74.0

688

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

83.0

361

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

119.

0489

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

130.

1120

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

144.

9533

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

189.

9538

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

190.

9458

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

223.

0452

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

365.

1975

ES+



of 13

Combine <5-54> Count 351Data Source Name 16010001_2015-30772_MSMS_365_20EV_50-400_1_Centroided Mass Spectrum_ES+Data Type Centroided Mass Spectrum Date 19 Jan 2016 17:26:40Date Stamp 19 Jan 2016 16:47:22 Estimated Molecular Ion 366.195File Name \\139.191.6.82\ihcp∴I01\Bio_Chemical_Interaction_Metabonomics\CLEN2SAND\!proposed-structure\BCIM_NAS\BCIM_

QTOF\16010001_2015-30772\16010001_2015-30772_MSMS_365_20EV_50-400.CDFInlet Model Electrospray Inlet Ion Mode ES+Plot Type Stick Retention Time 0.829Scan 45 Separation Type No ChromatographySpectrum Assigned 87.5% [50-400/0-100] TIC 225.77Total Signal 18373.9004

CH3

O

N

N

Retention Time: 0.829 Ion Mode: ES+

m/z3603403203002802602402202001801601401201008060

Rel

ativ

e In

tens

ity (%

)

0

5

10

15

20

25

30

35

40

45

50

55

60

65

70

75

80

85

90

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379

85.0

379 10

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

2510

5.04

25

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

134.

0619

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

146.

0613

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

178.

0826

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

188.

0990

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080

218.

1080 24

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

1424

4.12

14

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

281.

1484

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

365.

1968

ES+



of 13

Table of fragmentsNo. Fragment Structure Formula Label m/z Calc. TIC Calc.

(%)Difference

(Da)m/z Exp. RI Exp.

(%)TIC Exp.

(%)Origin

1 1-6 C+

5

O6

43

2CH3 1

C5H9O M - C19H23N2 85.065 0.540 -0.027 85.038 1.149 0.540 Manual

2 12-19

CH2+

1213

14

15

1617

18

19 C8H9 M - C16H23N2O 105.070 3.350 -0.027 105.043 6.917 3.350 Manual

3 5-8,22-27(+H2)

CH+

8 N75

O6

22

23 24

25

2627

C8H8NO M - C16H24N 134.060 1.165 0.002 134.062 2.392 1.165 Manual

4 7-10,21-27CH2

+

10 98

21

N7 22

2324

25

2627

C10H12N M - C14H20NO 146.096 0.819 -0.035 146.061 1.648 0.819 Manual

5 1-7,22-27(+H2) C11H16NO M - C13H16N 178.123 0.312 -0.040 178.083 0.619 0.312 Manual

6 8-21N11

109

CH+

82120

12

1314

1516

17

1819

C13H18N M - C11H14NO 188.143 51.427 -0.044 188.099 100.000 51.427 Manual

7 1-10,22-27(+H)

CH2 109 CH+

8N7

5

O6

22

23 24

25

2627

4

32

CH3 1

C14H20NO M - C10H12N 218.154 0.316 -0.046 218.108 0.605 0.316 Manual

8 1-10,20-27(-H)

10

9 8

21CH2

+

20

N7

5

O6

22

23 24

25

26274

32

CH3 1

C16H22NO M - C8H10N 244.170 2.672 -0.048 244.121 5.013 2.672 Manual

9 7-27(+H2) C19H25N2 M - C5H7O 281.201 2.943 -0.053 281.148 5.331 2.943 Manual

10 M(+H)NH

+11

10

9

821

20

1213

1415

16

17 18

19

N7

5O6

22

23 24

25

2627

4

3

2

CH31

C24H33N2O M + H 365.259 23.922 -0.062 365.197 40.879 23.922 Manual



of 13

Fragmentation of the observed molecule and the virtual MS (EI+) spectrum predicted byThermo Scientific Mass Frontier

5075

100

125

150

175

200

225

250

275

300

325

350

375

400

425

013253850637588100

273.

20

146.

10

189.

10

105.

10

274.

2057

.10

96.1

013

2.10

91.1

077

.10

42.0

011

8.10

147.

1019

0.10

70.1

023

0.20

172.

1024

4.20

335.

2036

3.20

307.

2032

1.20

215.

2026

4.20

415.

1040

1.00

N

N O

•

N

N O

•ON

N

ON

N

N

NH

NH

N

ON



of 13

Fragmentation of the observed molecule and the virtual MS and MSMS spectra predictedby Thermo Scientific Mass Frontier

5063

7588

100

113

125

138

150

163

175

188

200

213

225

238

250

263

275

288

300

313

325

338

350

363

375

388

400

013253850637588100

365.

20 366.

2160

.02

119.

0583

.03

144.

9518

9.95

130.

1274

.07

223.

05

367.

2110

2.01

208.

9526

2.02

171.

0615

7.98

244.

0829

3.96

311.

9634

4.86

278.

9333

1.02

387.

1835

7.91

96.0

2

N

N O

H

5063

7588

100

113

125

138

150

163

175

188

200

213

225

238

250

263

275

288

300

313

325

338

350

363

375

388

400

013253850637588100

188.

10

365.

20

189.

10

366.

2110

5.04

281.

1524

4.12

134.

0685

.04

160.

0717

8.08

218.

1157

.05

272.

1512

0.05

232.

1269

.04

96.0

519

7.61

374.

4935

7.56

307.

0825

7.91

393.

1833

4.99

321.

1029

0.07

N

N O

H

N 2H

N

N O

N O

NN 2

H

O

O

N O

NH

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