Extended data ESI+ 612 ESl+387 15 21 12 Con ES328 Con Meale.a 57 Con 43565758 Es|+387 Es-328 1314318 N flavescens Extended Data Figure 1. Analysis of hm-NAS clone families a,LCMS analysis of crude extracts prepared from E coli transformed with each hm-NAs gene expression construct(number 1-43, see Supplementary Table 1 for details about each clone number ) compared to negative control extracts derived from E. coli containing an empty vector(con). Based on metabolite retention time and observed mass hm-NAS genes could be grouped into 6 N-acyl amide families(1-6). The mass of the major metabolite (pictured) from each N-acyl amide family is shown in either the ESI(+)or ESI(-)MS detection mode for each hm-NAS extract including the control extract Functional Nature. Author manuscript; available in PMC 2018 February 28Extended Data Extended Data Figure 1. Analysis of hm-NAS clone families a, LCMS analysis of crude extracts prepared from E. coli transformed with each hm-NAS gene expression construct (number 1–43, see Supplementary Table 1 for details about each clone number) compared to negative control extracts derived from E. coli containing an empty vector (con). Based on metabolite retention time and observed mass hm-NAS genes could be grouped into 6 N-acyl amide families (1–6). The mass of the major metabolite (pictured) from each N-acyl amide family is shown in either the ESI(+) or ESI(−) MS detection mode for each hm-NAS extract including the control extract. Functional Cohen et al. Page 15 Nature. Author manuscript; available in PMC 2018 February 28. Author Manuscript Author Manuscript Author Manuscript Author Manuscript