1.0 2011-09-21 01:38:40 UTC 2015-07-21 06:59:23 UTC FDB028366 Geranylgeranylcysteine Geranylgeranylcysteine is a modified thioether amino acid in which an isoprenyl group (geranylgeranyl) has been attached to the sulfhydryl group of cysteine through a thioether bond. Geranylgeranylcysteine is typically formed through posttranslational (prenylation) protein modification whereupon degradation of the parent protein leaves the modified (prenylated) amino acid. Prenylation is a relatively recently discovered post-translational modification of proteins that directs cytosollic proteins to membranes while at the same time activating them functionally. The change in hydrophobicity that is essential for membrane binding is done via the covalent attachment of a polyisoprene (such as a farnesyl or geranylgeranyl group) to a C-terminal cysteine by a thioether bond. Prenylated proteins can comprise up to 2% of total cellular protein. Prenylcysteine lyase is an enzyme that is capable of cleaving the thiother bond in prenylcysteines and is used to help in the turnover of prenylated proteins. Prenylcysteine lyase deficiency leads to the accumulation of farnesylcysteine and geranylgeranylcysteine in brain and liver. (PMID: 9287348) [HMDB] S-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-(E,E,E)-L-Cysteine S-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]- (9CI)-L-Cysteine C23H37NO3S 407.61 407.249414745 (2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid (2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid 169523-06-2 SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1 UBCKUGRWFMEXIF-WONWMLGISA-N belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Acyclic diterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Diterpenoids Aliphatic acyclic compounds Alkylthiols Carbonyl compounds Carboxylic acids Cysteine and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl amines N-acyl-L-alpha-amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Acyclic diterpenoid Aliphatic acyclic compound Alkylthiol Alpha-amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cysteine or derivatives Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-acyl-l-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Secondary carboxylic acid amide Solid logp 5.58 ALOGPS logs -5.37 ALOGPS solubility 1.73e-03 g/l ALOGPS logp 5.65 ChemAxon pka_strongest_acidic 4.04 ChemAxon pka_strongest_basic 1.45 ChemAxon iupac (2R)-3-sulfanyl-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenamido]propanoic acid ChemAxon average_mass 407.61 ChemAxon mono_mass 407.249414745 ChemAxon smiles SC[C@H](NC(=O)\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O ChemAxon formula C23H37NO3S ChemAxon inchi InChI=1S/C23H37NO3S/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-22(25)24-21(16-28)23(26)27/h9,11,13,15,21,28H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H,26,27)/b18-11+,19-13+,20-15+/t21-/m0/s1 ChemAxon inchikey UBCKUGRWFMEXIF-WONWMLGISA-N ChemAxon polar_surface_area 66.4 ChemAxon refractivity 123.68 ChemAxon polarizability 48.79 ChemAxon rotatable_bond_count 13 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19527 Specdb::CMs 39761 Specdb::CMs 161047 Specdb::MsMs 309433 Specdb::MsMs 309434 Specdb::MsMs 309435 Specdb::MsMs 353857 Specdb::MsMs 353858 Specdb::MsMs 353859 Specdb::MsMs 2696739 Specdb::MsMs 2696740 Specdb::MsMs 2696741 Specdb::MsMs 2981393 Specdb::MsMs 2981394 Specdb::MsMs 2981395 HMDB11678 #<Reference:0x000055ce31d8c340> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823