1.0 2011-09-21 00:16:49 UTC 2015-07-21 06:57:16 UTC FDB022609 Pantetheine 4'-phosphate 4'-phosphopantetheine is a metabolite in the pantothenate and coenzyme A biosynthesis pathway. It can be generated from Pantatheine (via pantothenate kinase 1) or R-4'-Phospho-pantothenoyl-L-cysteine (via phosphopantothenoylcysteine decarboxylase) or Dephospho-CoA (via 4'-phosphopantetheine adenylyl-transferase and ectonucleotide pyrophosphatase). In most mammals, coenzyme A can be hydrolyzed to pantetheine and pantothenate in the intestinal lumen via the following series of reactions: coenzyme A leads to phosphopantetheine leads to pantetheine leads to pantothenate. The conversion of 4'-phosphopantetheine (4'-PP) to dephospho-CoA, is catalyzed by 4'-phosphopantetheine adenylyl-transferase. In mammalian systems, this step may occur in the mitochondria or in the cytosol. (PMID: 1746161) It has been identified as an essential cofactor in in the biosynthesis of fatty acids, polyketides, depsipeptides, peptides, and compounds derived from both carboxylic and amino acid precursors. In particular it is a key prosthetic group of acyl carrier protein (ACP) and peptidyl carrier proteins (PCP) and aryl carrier proteins (ArCP) derived from Coenzyme A. Phosphopantetheine fulfils two demands. Firstly, the intermediates remain covalently linked to the synthases (or synthetases) in an energy-rich thiol ester linkage. Secondly, the flexibility and length of phosphopantetheine chain (approximately 2 nm) allows the covalently tethered intermediates to have access to spatially distinct enzyme active sites. [HMDB] 4'-Opantetheine 4'-Opantotheine 4'-Phosphopantetheine 4'-phosphopantotheine D-Pantetheine 4'-ate D-Pantetheine 4'-phosphate O-Pantotheine Opantetheine Pantetheine 4'-ate Pantetheine 4'-ic acid Pantetheine 4'-phosphate Pantetheine 4'-phosphic acid Pantotheine-4'-ate Pantotheine-4'-ic acid pantotheine-4'-phosphate phospho-pantotheine Phosphopantetheine Psh-4'-P C11H23N2O7PS 358.348 358.096358302 [3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid pantetheine 4'-phosphate 2226-71-3 CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19) JDMUPRLRUUMCTL-UHFFFAOYSA-N belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Monoalkyl phosphates Organic compounds Organic acids and derivatives Organic phosphoric acids and derivatives Phosphate esters Aliphatic acyclic compounds Alkylthiols Carboximidic acids Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Secondary alcohols Alcohol Aliphatic acyclic compound Alkylthiol Carboximidic acid Carboximidic acid derivative Hydrocarbon derivative Monoalkyl phosphate Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Propargyl-type 1,3-dipolar organic compound Secondary alcohol phosphopantetheine Solid logp -0.71 ALOGPS logs -2.98 ALOGPS solubility 3.75e-01 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 1.79 ChemAxon pka_strongest_basic -1.5 ChemAxon iupac [3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid ChemAxon average_mass 358.348 ChemAxon mono_mass 358.096358302 ChemAxon smiles CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS ChemAxon formula C11H23N2O7PS ChemAxon inchi InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19) ChemAxon inchikey JDMUPRLRUUMCTL-UHFFFAOYSA-N ChemAxon polar_surface_area 145.19 ChemAxon refractivity 81.58 ChemAxon polarizability 34.28 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pantothenate and CoA Biosynthesis SMP00027 map00770 Specdb::CMs 2894 Specdb::CMs 38063 Specdb::MsMs 27113 Specdb::MsMs 27114 Specdb::MsMs 27115 Specdb::MsMs 33671 Specdb::MsMs 33672 Specdb::MsMs 33673 Specdb::NmrOneD 315401 Specdb::NmrOneD 315402 Specdb::NmrOneD 315403 Specdb::NmrOneD 315404 Specdb::NmrOneD 315405 Specdb::NmrOneD 315406 Specdb::NmrOneD 315407 Specdb::NmrOneD 315408 Specdb::NmrOneD 315409 Specdb::NmrOneD 315410 Specdb::NmrOneD 315411 Specdb::NmrOneD 315412 Specdb::NmrOneD 315413 Specdb::NmrOneD 315414 Specdb::NmrOneD 315415 Specdb::NmrOneD 315416 Specdb::NmrOneD 315417 Specdb::NmrOneD 315418 Specdb::NmrOneD 315419 Specdb::NmrOneD 315420 HMDB01416 16858 1H1T #<Reference:0x000055ce334ae730> 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 Acyl carrier protein, mitochondrial O14561 NDUFAB1 Bifunctional coenzyme A synthase Q13057 COASY Fatty acid synthase P49327 FASN Mitochondrial 10-formyltetrahydrofolate dehydrogenase Q3SY69 ALDH1L2 Pantothenate kinase 1 Q8TE04 PANK1 Pantothenate kinase 3 Q9H999 PANK3 Pantothenate kinase 4 Q9NVE7 PANK4