Supporting Information
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1 Supporting Information Structure Based ptimization of Potent and Selective Inhibitors of the Tyrosine Kinase EphB4 Karine Lafleur, Danzhi Huang,, Ting Zhou, Amedeo Caflisch,, and Cristina evado, Department of Biochemistry, Department of rganic Chemistry, University of Zürich, Winterthurerstrasse 19, CH-857, Zürich, Switzerland Table of contents S1 S2 to S6 S7 S8 S9 S1 to S13 S14 to S76 S77 to S82 Title Page Selectivity data Conformational analysis data Time series of van der Waals and electrostatic interaction energies SAR-based dendrogram Experimental Procedures 1 H-MR and 13 C-MR of selected compounds LC trace (for purity) of tested compounds To whom correspondence should be addressed. Phone: (41) Fax: (41) dhuang@bioc.uzh.ch, caflisch@bioc.unizh.ch, nevado@oci.uzh.ch Dept. of Biochemistry Dept. of rganic Chemistry S1
2 Table S1. Local selectivity of compound 66. These IC 5 values were measured at the University of Dundee. Percentage of kinase activity compared to a Kinases 1% DMS control 54 a 66 b MKK1 7 7 ERK ERK JK JK p38a MAPK p38b MAPK p38g MAPK p38d MAPK ERK RSK RSK PDK PKBa PKBb SGK S6K PKA RCK PRK PKCa PKCz PKD MSK MK MK MAPKAP-K PRAK CAMKKb CAMK SmMLCK PHK S2
3 CHK CHK GSK3b CDK2-Cyclin A 97 9 PLK Aurora B AMPK MARK BRSK MELK 89 8 CK CK DYRK1A DYRK DYRK EK2a EK IKKb PIM PIM PIM SRPK MST EF2K HIPK PAK PAK PAK Src 12 9 Lck 3 CSK FGF-R IRR 11 1 EPHA2 1 7 MST SYK YES1 6 3 S3
4 IGF-1R VEG-FR BTK IR-HIS EPHB TBK IKKe GCK IRAK UAK MLK MIK MLK LKB HER TTK a Percentage of 3μM concentration of compound 54 b Percentage of 1μM concentration of compound 66 S4
5 Table S2. Selectivity of compound 66 on kinases predicted to have a small gatekeeper. These IC 5 values were measured at Ambit Biosciences Corporation. Kinases Percentage of kinase remaining bound to the beads, relative to a 1% DMS control a ABL1-phosphorylated.15 ABL2.75 ALK 99 BLK.6 BMPR1A 51 BMPR1B.9 BMX 55 BRK 12 DDR1 1.4 DDR2 21 EGFR 8.6 EPHA6 4 EPHB4 1.2 EPHB6 32 ERBB2 27 ERBB3 78 FGFR2 94 FGFR3 89 FGFR4 1 FLT4 93 FRK.3 FY.25 GAK 49 GC2(Kin.Dom.2,S88G) 1 HCK.6 KIT 88 LIMK1 83 LIMK2 78 LY.4 EK11 67 LK 83 PDGFRA 84 PDGFRB 53 S5
6 QSK 32 RAF1 14 RET 79 RIPK2 2.9 RSK3(Kin.Dom.2-Cterminal) 84 RSK4(Kin.Dom.2-Cterminal) 5.8 SIK 41 SRMS 18 TEC 1 TESK1 9.8 TGFBR1 3.6 TGFBR2 2.4 VEGFR2 96 YAK1 8 YAK2 89 YAK3 1 ZAK 15 a Percentage of 1μM concentration of compound 66 S6
7 15 15 γ2 γ _local_minima 4_docked_conformation γ1 54_local_minima 54_docked_conformation γ γ2 γ _local_minima 6_docked_conformation γ1 66_local_minima 66_docked_conformation γ S7 Figure S1. Conformational analysis on 4, 54, 6, 66. The local minima obtained by ab initio minimization of each rotameric state are plotted against the dihedral angles γ1 and γ2 (blue). The global minima are indicated in red.
8 Figure S2. Time series of the van der Waals and electrostatic interaction energies between the methyl of compound 66 and the side chains of Val629, Ala645 and Thr693. S8
9 AAK1 BIKE CK2a1 LKB1 AurC SRPK1 PLK4 MPSK1 CK1d CK1e GAK 49. CLK1 CLK4 CLK2 DRAK1 DRAK2 MK2 TTK JK1 JK3 ZC2-TIK FLT1 FMS FLT3 KIT 88. PDGFRa 84. PDGFRb 53. LK SLK AurA AurB TK1 FLT4 93. RET 79. CDK2 PCTAIRE1 GSK3A CDK5 skmlck JAK1 Fused PIM1 PIM2 DAPK2 DAPK3 CK1a2 CK1g CLK3 ALK AXL MER MST2 MST1 MET HPK1 KHS2 LTK KHS1 TIE2 RS MAP3K4 CK1g2 SYK EphA7 STK33 CaMKK2 PHKg2 ZC1-HGK MRCKa ACTR2B ACTR2 ALK1 ALK2 BMPR1A ALK4 TGFbR1 BRSK2 ABL EphA2 EphA4 EphB2 EphB4 EphA6 EphB3 HH498 ACK SRC BLK LCK YES HCK FGR FY FRK BRK RIPK2 ARG EphA1 EphA5 EphA8 EphB1 EphA3 CSK LY BRAF RAF1 KDR FGFR1 FGFR2 FGFR3 FGFR4 LIMK2 BMX BTK LIMK1 EGFR HER2-ErbB2 HER4-ErbB4 PLK3 PLK1 EK2 EK9 EK6 EK7 YAK3 YAK2 p38b p38a LK JK2 p38g TESK1 TYR3 TXK MLK Pourcentage of kinase activity compared to a 1% DMS control. These values were measured at Reaction Biology Corporation (black), at the University of Dundee (green) and at Ambit Biosciences Corporation (blue). MUSK TRKB TRKC TRKA TLK1 TLK2 MYT1 MAP3K5 MARK2 MST3 MST4 CaMK1a CaMK1d AKT1 AKT ZAP7 PRKX PKACa PKACb PKG1 PKG2 PKCh PK2 DR2 Erk1 Erk2 MSK1 MSK2 RSK2 RSK1 PAK2 RSK4 QIK PDK1 AMPKa1 AMPKa2 CK2a2 MARK4 MARK1 PAK3 PHKg1 CaMK2a CaMK2b CaMK2d CaMK2g DMPK1 PYK2 ITK PAK4 PAK5 PAK6 IGF1R ISR IRR FAK FES AKT2 PAK1 YSK1 CaMK1g FER Figure S3. SAR-based dendrogram. S9
10 6-Amino-1-methyl-2,4(1H,3H)-pyrimidinedione (5) A mixture of methylurea (22.4 g, 32 mmol), 2-cyanoacetic acid (38. g, 447 mmol) and Ac 2 (74 ml) was heated to 6 C for 2.5 h. After cooling to room temperature, water (74 ml) was added, and the suspension was stirred for 1 h. The solid intermediate was filtered, suspended in ah (2%, 15 ml), and heated to 9 C for 1 h. The reaction mixture was then cooled to 2 C, acidified with concentrated HCl, and the precipitate was collected by filtration (27.2 g, 64% yield) as a light yellow solid. 1 H MR (4 MHz, DMS-d 6 ): = 1.43 (s, 1H), 6.88 (s, 2H), 4.61 (s, 1H), 3.18 (s, 3H); IR (film): ~ = 3344, 3183, 311, 346, 166, 1618, 1548, 1276, 1161, 827 cm -1 ; MS (ESI): m/z: calcd for C 5 H 7 3 a 2 : 164., found: 164. [M + a] +. 6-Amino-1-(phenylmethyl)-2,4(1H,3H)-pyrimidinedione (6) A mixture of benzylurea (5. g, 33.3 mmol), 2-cyanoacetic acid (2.6 g, mmol) and Ac 2 (2 ml) was heated at 8 C for 2 h. After cooling to room temperature, Et 2 (3 ml) was added, and the resultant suspension was stirred for 1 h. The solid intermediate was filtered, suspended in a mixture of water (3 ml) and ethanol (15 ml) and heated at 85 C. ah (1%, 5 ml) were slowly added. After 1 h, the reaction mixture was concentrated, acidified with concentrated HCl, and the precipitate collected by filtration. If necessary, the solid was washed with acetone to afford a light yellow solid (3.5 g, 49% yield). 1 H MR (4 MHz, DMS-d 6 ): = 1.44 (s, 1H), (m, 5H), 6.75 (s, 2H), 5.2 (s, 2H), 4.59 (d, J = 2. Hz, 1H); 13 C MR (75 MHz, DMS-d 6 ): = 162.3, 155.7, 151.4, 136.6, 128.4, 127.1, 126.2, 75.5, 43.5; IR (film): ~ = 347, 3327, 325, 3217, 37, 2968, 2766, 1694, 163, 1575, 1494, 1384, 1278, 895, 821, 728 cm -1 ; MS (ESI): m/z: calcd for C 11 H 11 3 a 2 : 24.1, found: 24.1 [M + a] +. General procedure for the preparation of 1-alkyl-5-nitroso-4-aminouracil (7, 8) To a stirred mixture containing 1-alkyl-6-aminouracil (1 eq) in water (.45 M) and acetic acid (8.2 M) at -5 ºC, a 2 (1.1 eq) was added in small portions. A deep purple color, characteristic of the nitroso derivative appeared immediately, and stirring was continued at room temperature S1
11 for 19 h. The solid was filtered off, washed with cold water, and dried under high vacuum to obtain the corresponding products in pure form. 6-Amino-1-methyl-5-nitroso-2,4(1H,3H)-pyrimidinedione (7) Yield: 77%; 1 H MR (3 MHz, DMS-d 6 ): = 13.2 (s, 1H), (s, 1H), 9.14 (s, 1H), 3.19 (s, 3H); 13 C MR (1 MHz, DMS-d 6 ): = 16.2, 148.7, 147.5, 138.6, 27.8; IR (film): ~ = 327, 3225, 38, 325, 17, 1568, 151, 1427, 1395, 1233, 117, 121, 866, 72 cm -1 ; MS (ESI): m/z: calcd for C 5 H 6 4 a 3 : 193., found: 193. [M + a] +. 6-Amino-5-nitroso-1-(phenylmethyl)-2,4(1H,3H)-pyrimidinedione (8) Yield: 93%; 1 H MR (4 MHz, DMS-d 6 ): = (s, 1H), (s, 1H), 9.12 (s, 1H), (m, 5H), 5.8 (s, 2H); 13 C MR (75 MHz, DMS-d 6 ): = 16.4, 148.9, 146.9, 138.6, 134.6, 128.6, 127.4, 126.3, 43.3; IR (film): ~ = 3145, 2969, 2773, 1729, 1691, 1636, 159, 1448, 141, 1247, 1161, 725 cm -1 ; MS (ESI): m/z: calcd for C 11 H 1 4 a 3 : 269.1, found: 269. [M + a] +. General procedure for the preparation of 1-alkyl-5,6-diaminouracil (9, 1) To a stirred mixture containing 1-alkyl-5-nitroso-4-aminouracil (1 eq) in aqueous ammonia (25%,.6 M), sodium dithionite (3.5 eq) was added in small portions. The temperature raised to 35 C and the purple color disappeared gradually. When no more temperature increase was observed, the reaction mixture was stirred at 6 C for an additional hour and then 17 h at room temperature in order to complete the reaction (total disappearance of the purple color). The solid was filtered off, thoroughly washed with cold water, and dried under high vacuum to obtain the corresponding products in pure form. 5,6-Diamino-1-methyl-2,4(1H,3H)-pyrimidinedione (9) S11
12 Yield: 78%; 1 H MR (4 MHz, DMS-d 6 ): = 1.53 (s, 1H), 6.12 (s, 2H), 3.21 (s, 3H), 2.95 (s, 2H); IR (film): ~ = 3351, 3313, 3148, 1667, 1636, 1579, 159, 962, 712 cm -1 ; MS (ESI): m/z: calcd for C 5 H : 157.1, found: 157. [M + H] +. 5,6-Diamino-1-(phenylmethyl)-2,4(1H,3H)-pyrimidinedione (1) Yield: 9%; 1 H MR (4 MHz, DMS-d 6 ): = 9.88 (s, 1H), (m, 5H), 6.9 (s, 2H), 5.7 (s, 2H), 2.92 (s, 2H); 13 C MR (75 MHz, DMS-d 6 ): = 159.6, 149.6, 145.3, 136.8, 128.3, 127., 126.4, 96.4, 43.9; IR (film): ~ = 346, 335, 3183, 2968, 2776, 1686, 1628, 1574, 1496, 142, 942, 717 cm -1 ; MS (ESI): m/z: calcd for C 11 H 12 4 a 2 : 255.1, found: [M + a] +. 3,9-Dihydro-3-methyl-1H-purine-2,6-dione (11) A solution of 1-methyl-5,6-diaminouracil (18.8 g, 12 mmol) in formic acid (6.2 ml) and water (14 ml) was heated to reflux for 3 h. After cooling to 2 C, ah (9.6 g, 24 mmol) in water (12 ml) was added, and the mixture was heated to reflux for 1 h. After cooling to C, the mixture was acidified by addition of acetic acid. The precipitate was filtered, washed with water, and dried to afford 11 as a light yellow solid (15.5 g, 78% yield). 1 H MR (3 MHz, DMSd 6 ): = 11.9 (s, 1H), 8.4 (s, 1H), 3.37 (s, 3H), 7 H not observed; 13 C MR (1 MHz, DMS-d 6 ): = 154.6, 151.1, 149.2, 14.2, 16.9, 28.8; IR (film): ~ = 3371, 312, 311, 1689, 141, 1164, 827, 742 cm -1 ; MS (ESI): m/z: calcd for C 6 H : 167.1, found: 167. [M + H] +. 3,9-Dihydro-3-(phenylmethyl)-1H-purine-2,6-dione (12) A solution of 1-benzyl-5,6-diaminouracil (761 mg, 3.28 mmol) in formic acid (15 ml) was heated to reflux for 1 h and then the formic acid was evaporated under reduced pressure. The residue was dissolved in aqueous ah (1%, 15 ml) and ethanol (5 ml). The mixture was heated to reflux for 1 h, and then concentrated. After cooling to C, the mixture was acidified by addition of concentrated HCl. The precipitate was filtered, washed with water, and dried to afford 12 as a light yellow solid (714 mg, 9% yield). 1 H MR (4 MHz, DMS-d 6 ): = S12
13 (s, 1H), (s, 1H), 8.1 (s, 1H), (m, 5H), 5.11 (s, 2H); 13 C MR (75 MHz, DMSd 6 ): = 154.6, 15.9, 149.1, 14.6, 137., 128.3, 127.4, 127.1, 17., 44.9; IR (film): ~ = 3145, 2986, 296, 1662, 1551, 1414, 126, 165, 73 cm -1 ; MS (ESI): m/z: calcd for C 12 H 1 4 a 2 : 265.1, found: 265. [M + a] +. General procedure for the bromination of 3-alkylxanthines (13, 14) To a stirring suspension of 3-alkylxanthine (1 eq) and sodium acetate (2 eq) in glacial acetic acid (.39 M) was added bromine dropwise (1.2 eq). The mixture was stirred at 65 C for 2 h. After cooling to room temperature the precipitate was filtered, washed with acetic acid, water, and dried under vacuum to give the corresponding 3-alkyl-8-bromoxanthine as beige powders in pure form. 8-omo-3,9-dihydro-3-methyl-1H-purine-2,6-dione (13) Yield: 84%; 1 H MR (3 MHz, DMS-d 6 ): = (s, 1H), 3.31 (s, 3H), 7 H not observed; 13 C MR (75 MHz, DMS-d 6 ): = 153.6, 15.7, 149.4, 124.1, 19.7, 28.8; IR (film): ~ = 3577, 3362, 329, 2968, 2832, 1667, 1468, 1268, 861, 748 cm -1 ; MS (ESI): m/z: calcd for C 6 H : 244.9, found: [M + H] +. 8-omo-3,9-dihydro-3-(phenylmethyl)-1H-purine-2,6-dione (14) Yield: 73%; 1 H MR (4 MHz, DMS-d 6 ): = (s, 1H), (m, 5H), 5.6 (s, 2H), 7 H not observed; 13 C MR (1 MHz, DMS-d 6 ): = 153.8, 15.6, 149.2, 136.8, 128.4, 127.3, 127.2, 124.7, 11.1, 45.1; IR (film): ~ = 327, 285, 2817, 172, 1667, 1541, 146, 1368, 134, 739 cm -1 ; MS (ESI): m/z: calcd for C 12 H : 32.9, found: [M + H] +. S13
14 H H S14
15 H H H H S15
16 H H H H S16
17 H H H H S17
18 H H 2 H S18
19 H H 2 H H H 2 H S19
20 H H H H S2
21 S H H H H 12 12
22 H 13 H H 13 H S22
23 S H H H H 14 14
24 S H H 16 16
25 S
26 S
27 S
28 S H H 22 22
29 S H H 23 23
30 S H H 24 24
31 S H H 25 25
32 S H H 26 26
33 S H F H F 27 27
34 S H H
35 S H H 29 29
36 S H H 3 3
37 S H H 31 31
38 S H H 32 32
39 S H H 33 33
40 S H H 34 34
41 S H H 35 35
42 S H H 36 36
43 S H H H H 37 37
44 S H H H H 38 38
45 S H H H H 39 39
46 S H H H H 4 4
47 S H H H H 41 41
48 S H H H H 42 42
49 S H H H H H H 43 43
50 S H C H C 44 44
51 S H H 45 45
52 S H F H F 46 46
53 S H H
54 S H H 48 48
55 S H H H H 49 49
56 S H H 5 5
57 S H H 51 51
58 S H H 52 52
59 S H 53
60 S H H 54 54
61 S H H 55 55
62 S H H 56 56
63 S H H 57 57
64 S H H H H 58 58
65 S H H H H 59 59
66 S H H H H 6 6
67 S H H H H 61 61
68 S H H H H 62 62
69 S H H H H 63 63
70 S H H H H 64 64
71 S H H 65
72 S H H H H 66 66
73 S H H H H H H 67 67
74 S H H 68 68
75 S H H F H H F 69 69
76 S H C 2 H H C 2 H 7 7
![5 min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % ---- ------- ---- ------- ---------- ---------- -------- 1 12.992 BB.128 1.4679e4 1695.](/docs-images/92/109439512/images/77-2.jpg "99756 99.2969 2 14.933 BV.1175 67.43863 8.41861.476 3 15.315 VB.1172 32.1753 4.2817.2271 Totals : 1.41675e4 178.44434 Results obtained with enhanced integrator!")
77 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2182ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % PB e BB BP Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2183ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % BB e BV VB Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2111ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MM e MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2115ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF FM MF e FM Totals : 1.429e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2116ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MM e Totals : e Results obtained with enhanced integrator! S77
![5 min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % ---- ------- ---- ------- ---------- ---------- -------- 1 1.21 MM.1267 111.57723 14.](/docs-images/92/109439512/images/78-3.jpg "67663.7232 2 11.76 MM.1322 1.53173e4 1931.68738 99.2768 Totals : 1.54289e4 1946.3641 Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2119ELC.D) mau 15 11.28 1 5 1.126 11.")
78 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2123ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e MM Totals : 2.16e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2118ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2119ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e MM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\212ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2113ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MF e FM MM Totals : e Results obtained with enhanced integrator! S78
79 mau DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2124ELC.D) Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF e FM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2125ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MF MF e FM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2117ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2122ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF e FM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2128ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MM e MM MM Totals : 2.311e Results obtained with enhanced integrator! S79
80 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2114ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MF e FM MM MM Totals : e Results obtained with enhanced integrator! mau 15 1 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2121ELC.D) min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM e MM MM MM MM Totals : 1.527e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2126ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM e MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2127ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM e MM MM MM Totals : e Results obtained with enhanced integrator! mau 15 1 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2131ELC.D) min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF e FM MM Totals : e Results obtained with enhanced integrator! S8
81 mau 15 1 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2129ELC.D) min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF e FM MM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\213ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MF e FM MM MM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2132ELC.D) mau min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM e FM MM MM MM Totals : e Results obtained with enhanced integrator! DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2187ELC.D) mau Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % PB BB BB BB BV VB VV Totals : e Results obtained with enhanced integrator! mau 6 4 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2184ELC.D) min Signal 1: DAD1 A, Sig=254,8 Ref=4,1 Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % BB VV VP Totals : Results obtained with enhanced integrator! S81
82 mau 6 4 DAD1 A, Sig=254,8 Ref=4,1 (SERVICE\2112ELC.D) Signal 1: DAD1 A, Sig=254,8 Ref=4,1 min Peak RetTime Type Width Area Height Area # [min] [min] [mau*s] [mau] % MM MM MM MM MM MM Totals : Results obtained with enhanced integrator! S82
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