<p> SUPPORTING INFORMATION</p><p>Mooreamide: A Cannabinomimetic Lipid from the Marine Cyanobacterium</p><p>Moorea bouillonii</p><p>Emily Mevers, Teatulohi Matainaho, Marco Allara’, Vincenzo Di Marzo and William H.</p><p>Gerwick</p><p>NMR Spectroscopic Data and Biological Data for Mooreamide (1)</p><p>1 Figure S1 H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)</p><p>13 Figure S2 C NMR (125 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1 Figure S3 HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1 Figure S4 HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1 Figure S5 COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1) </p><p>1 Figure S6 NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1) Figure S7 Displacement of [3H]-CP 55,940 by mooreamide (1) 1 Figure S1: H NMR (500 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1782H-2_3-A-5-G STANDARD PROTON PARAMETERS 1100</p><p>1000</p><p>900</p><p>800</p><p>700</p><p>600</p><p>500</p><p>400</p><p>300</p><p>200</p><p>100</p><p>0</p><p>-100</p><p>7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 f1 (ppm) 13 Figure S2: C NMR (125 MHz, CDCl3) spectrum of mooreamide (1) 9 5 5 0 0 2 6 0 1 6 6 1 9 1 0 5 9 1 6 8 9 1 4 4 4 3 8 2 7 6 0 3 8 4</p><p>1782H-2_3-A-5-G_CDCl3_vx500MHz 1 ...... 13 9 1 8 7 8 0 0 4 8 7 5 5 0 7 5 9 6 2 0 9 6 4 1 4 ...... 6 4 3 3 3 3 2 2 2 2 1 3 2 9 3 2 2 1 9 8 8 8 6 Std carbon 0 1 1 1 1 1 1 1 1 1 1 1 6 5 3 3 3 3 3 2 2 2 2 1 -</p><p>12</p><p>11</p><p>10</p><p>9</p><p>8</p><p>7</p><p>6</p><p>5</p><p>4</p><p>3</p><p>2</p><p>1</p><p>0</p><p>-1</p><p>170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 0 -10 f1 (ppm) 1 Figure S3: HSQC ( H 500 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1782H-2_3-A-5-G_gHSQC STANDARD PROTON PARAMETERS 10</p><p>20</p><p>30</p><p>40</p><p>50</p><p>60</p><p>70 ) m p p ( 80 1 f</p><p>90</p><p>100</p><p>110</p><p>120</p><p>130</p><p>140</p><p>150 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S4: HMBC ( H 600 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1782H2/2 HMBC (hmbcgplpndqf) 10 Cryoprobe 062708 20</p><p>30</p><p>40</p><p>50</p><p>60</p><p>70</p><p>80 ) m p p (</p><p>90 1 f 100</p><p>110</p><p>120</p><p>130</p><p>140</p><p>150</p><p>160</p><p>170</p><p>6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 f2 (ppm) 1 Figure S5: COSY ( H 500 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1782H-23-A-56-gCOSY STANDARD PROTON PARAMETERS 0.5</p><p>1.0</p><p>1.5</p><p>2.0</p><p>2.5</p><p>3.0 ) m p</p><p>3.5 p (</p><p>1 f 4.0</p><p>4.5</p><p>5.0</p><p>5.5</p><p>6.0</p><p>6.5</p><p>6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) 1 Figure S6: NOESY ( H 600 MHz, CDCl3) spectrum of mooreamide (1)</p><p>1782H2/5 0.5 NOESY (noesyph) Cryoprobe 062708 1.0</p><p>1.5</p><p>2.0</p><p>2.5</p><p>3.0</p><p>3.5</p><p>4.0</p><p>4.5</p><p>5.0</p><p>5.5</p><p>6.0</p><p>6.5</p><p>6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 f2 (ppm) Figure S7: Displacement of [3H]-CP 55,940 by mooreamide (1).</p><p> g 100 n f i o d t n i n</p><p> b 75 e</p><p>0 m 4 e 9 c , a 5 50 l 5 p s P i d C</p><p>- 25 ] % H 3 [ 0 -10 -8 -6 -4 log[M]</p>