1.0 2016-09-30 22:39:12 UTC 2020-05-21 16:28:57 UTC BMDB0000961 BMDB00961 Farnesyl pyrophosphate Farnesyl pyrophosphate, also known as farnesyl pyrophosphate or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Farnesyl pyrophosphate exists in all living species, ranging from bacteria to humans. In cattle, farnesyl pyrophosphate is involved in the metabolic pathway called the porphyrin metabolism pathway. (2E,6E)-Farnesol diphosphate (2E,6E)-Farnesyl diphosphate (2E,6E)-Farnesyl pyrophosphate (all-e)-Farnesyl diphosphate (e,e)-Farnesyl pyrophosphate 2-trans,6-trans-Farnesyl pyrophosphate all-trans-Farnesyl pyrophosphate Farnesyl diphosphate trans,trans-Farnesyl diphosphate trans-trans-Farnesyl diphosphate 2-trans,6-trans-Farnesyl diphosphate (2E,6E)-Farnesol diphosphoric acid (2E,6E)-Farnesyl diphosphoric acid (2E,6E)-Farnesyl pyrophosphoric acid (all-e)-Farnesyl diphosphoric acid (e,e)-Farnesyl pyrophosphoric acid 2-trans,6-trans-Farnesyl pyrophosphoric acid all-trans-Farnesyl pyrophosphoric acid Farnesyl diphosphoric acid trans,trans-Farnesyl diphosphoric acid trans-trans-Farnesyl diphosphoric acid 2-trans,6-trans-Farnesyl diphosphoric acid Farnesyl pyrophosphoric acid (e,e)-Farnesyl diphosphate Farnesyl-PP trans-Farnesyl pyrophosphate trans-trans-Farnesyl pyrophosphate Farnesyl pyrophosphate, (e,e)-isomer Farnesyl pyrophosphate, (e,Z)-isomer Farnesyl pyrophosphate, (Z,e)-isomer Farnesyl pyrophosphate, (Z,Z)-isomer Farnesylpyrophosphate C15H28O7P2 382.33 382.131027238 {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid farnesyl diphosphate 13058-04-3 [H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+ VWFJDQUYCIWHTN-YFVJMOTDSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Sesquiterpenoids Hydrocarbon derivatives Isoprenoid phosphates Monoalkyl phosphates Organic oxides Organic pyrophosphates Organooxygen compounds Aliphatic acyclic compound Alkyl phosphate Farsesane sesquiterpenoid Hydrocarbon derivative Isoprenoid phosphate Monoalkyl phosphate Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organooxygen compound Phosphoric acid ester Sesquiterpenoid Aliphatic acyclic compounds Acyclic farnesane sesquiterpenoids Acyclic farnesane sesquiterpenoids Farnesenes farnesyl diphosphate Solid logp 2.40 ALOGPS logs -3.68 ALOGPS logp 3.62 ChemAxon pka_strongest_acidic 1.77 ChemAxon iupac {[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid ChemAxon average_mass 382.33 ChemAxon mono_mass 382.131027238 ChemAxon smiles [H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C ChemAxon formula C15H28O7P2 ChemAxon inchi InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+ ChemAxon inchikey VWFJDQUYCIWHTN-YFVJMOTDSA-N ChemAxon polar_surface_area 113.29 ChemAxon refractivity 96.73 ChemAxon polarizability 37.94 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Porphyrin Metabolism SMP0087243 Steroid Biosynthesis SMP0087233 Specdb::MsMs 24932 Specdb::MsMs 24933 Specdb::MsMs 24934 Specdb::MsMs 31490 Specdb::MsMs 31491 Specdb::MsMs 31492 Specdb::MsMs 1471330 Specdb::MsMs 1473174 Specdb::MsMs 1473175 Specdb::MsMs 1473176 Specdb::MsMs 1473177 Specdb::MsMs 1473178 Specdb::MsMs 1473179 Specdb::MsMs 1473180 Specdb::MsMs 1473404 Specdb::MsMs 2739028 Specdb::MsMs 2739029 Specdb::MsMs 2739030 Specdb::MsMs 2969821 Specdb::MsMs 2969822 Specdb::MsMs 2969823 Specdb::CMs 2694 Specdb::CMs 173893 Specdb::NmrOneD 308731 Specdb::NmrOneD 308732 Specdb::NmrOneD 308733 Specdb::NmrOneD 308734 Specdb::NmrOneD 308735 Specdb::NmrOneD 308736 Specdb::NmrOneD 308737 Specdb::NmrOneD 308738 Specdb::NmrOneD 308739 Specdb::NmrOneD 308740 Specdb::NmrOneD 308741 Specdb::NmrOneD 308742 Specdb::NmrOneD 308743 Specdb::NmrOneD 308744 Specdb::NmrOneD 308745 Specdb::NmrOneD 308746 Specdb::NmrOneD 308747 Specdb::NmrOneD 308748 Specdb::NmrOneD 308749 Specdb::NmrOneD 308750 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00448 FDB022339 393270 DB07780 17407 445713 C00007268 FARNESYL-PP Farnesyl pyrophosphate 35006 403 Castillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. University of California, San Francisco., 1977 - Farnesol  p.364 BMDBP00261 Squalene synthase Q32KR6 FDFT1 Enzyme BMDBP00940 Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P29702 FNTA Enzyme BMDBP00941 Protein farnesyltransferase subunit beta P49355 FNTB Enzyme BMDBP02956 Protoheme IX farnesyltransferase, mitochondrial A5D7D6 COX10 Enzyme