Lipid compounds and lipid nanoparticle compositions

A compound of Formula (I):

• or a pharmaceutically acceptable salt, prodrug or stereoisomer thereof, wherein:
• G1 and G2 are each independently a bond, C2-C12 alkylene, or C2-C12 alkenylene;
• L1 is —OC(═O)R1, —C(═O)OR′, —OC(═O)OR′, —C(═O)R1, —OR′, —S(O)xR1, —S—SR1, —C(═O)SR1, —SC(═O)R1, —NRaC(═O)R1, —C(═O)NRbRc, —NRaC(═O)NRbRc, —OC(═O)NRbRc, —NRaC(═O)OR1, —SC(═S)R1, —C(═S)SR′, —C(═S)R1, —CH(OH)R1, —P(═O)(ORb)(ORc), —(C6-C10 arylene)-R1, -(6- to 10-membered heteroarylene)-R1, or R1;
• L2 is —OC(═O)R2, —C(═O)OR2, —OC(═O)OR2, —C(═O)R2, —OR2, —S(O)xR2, —S—SR2, —C(═O)SR2, —SC(═O)R2, —NRdC(═O)R2, —C(═O)NReRf, —NRdC(═O)NReRf, —OC(═O)NReRf, —NRdC(═O)OR2, —SC(═S)R2, —C(═S)SR2, —C(═S)R2, —CH(OH)R2, —P(═O)(ORe)(ORf), —(C6-C10 arylene)-R2, -(6- to 10-membered heteroarylene)-R2, or R2;
• R1 and R2 are each independently C6-C24 alkyl or C6-C24 alkenyl;
• Ra, Rb, Rd, and Re are each independently H, C1-C12 alkyl, or C2-C12 alkenyl;
• Rc and Rf are each independently C1-C12 alkyl or C2-C12 alkenyl;
• G3 and G4 are each independently C1-C12 alkylene;
• L3 and L4 are each independently —OC(═O)—, —C(═O)O—, —OC(═O)O—, —C(═O)—, —O—, —S(O)x—, —S—S—, —C(═O)S—, —SC(═O)—, —NRaC(═O)—, —C(═O)NRb—, —NRaC(═O)NRO—, —OC(═O)NRb—, —NRaC(═O)O—, —SC(═S)—, —C(═S)S—, —C(═S)—, —CH(OH)—, —P(═O)(ORb)O—, —(C6-C10 arylene)-, or -(6- to 10-membered heteroarylene)-;
• G5 is C2-C24 alkylene, C2-C24 alkenylene, C3-C8 cycloalkylene, or C3-C8 cycloalkenylene;
• R3 is —N(R4)R5 or —OR6;
• R4 is hydrogen, C1-C12 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C6-C10 aryl;
• R5 is C1-C12 alkyl;
• or R4 and R5 together with the nitrogen to which they are attached form a cyclic moiety;
• R6 is hydrogen, C1-C12 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, or C6-C10 aryl;
• x is 0, 1, or 2;
• n is 1, 2, or 3;
• m is 1, 2, or 3;
• and
• wherein each alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkylene, alkenylene, cycloalkylene, cycloalkenylene, arylene, heteroarylene, and cyclic moiety is independently optionally substituted.