1.0 2011-09-21 01:53:21 UTC 2015-07-21 06:59:40 UTC FDB029290 Undecanoyl-CoA Undecanoyl coA is a acyl-CoA with the C-11 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. [HMDB] C32H56N7O17P3S 935.81 935.266623627 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N InChI=1S/C32H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-23(41)60-16-15-34-22(40)13-14-35-30(44)27(43)32(2,3)18-53-59(50,51)56-58(48,49)52-17-21-26(55-57(45,46)47)25(42)31(54-21)39-20-38-24-28(33)36-19-37-29(24)39/h19-21,25-27,31,42-43H,4-18H2,1-3H3,(H,34,40)(H,35,44)(H,48,49)(H,50,51)(H2,33,36,37)(H2,45,46,47)/t21-,25-,26-,27?,31-/m1/s1 IZWCGXGZGYKDHR-WMMBNDHFSA-N belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain. 2,3,4-saturated fatty acyl CoAs Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl thioesters Aromatic heteropolycyclic compounds 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Beta amino acids and derivatives Carbonyl compounds Carbothioic S-esters Coenzyme A and derivatives Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Medium-chain fatty acyl CoAs Monoalkyl phosphates Monosaccharide phosphates N-acyl amines N-substituted imidazoles Organic oxides Organic pyrophosphates Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Tetrahydrofurans Thioesters 6-aminopurine Alcohol Alkyl phosphate Amine Amino acid or derivatives Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Beta amino acid or derivatives Carbonyl group Carbothioic s-ester Carboxamide group Carboxylic acid derivative Coenzyme a or derivatives Fatty amide Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-acyl-amine N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Oxacycle Pentose monosaccharide Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Pyrimidine Ribonucleoside 3'-phosphate Secondary alcohol Secondary carboxylic acid amide Sulfenyl compound Tetrahydrofuran Thiocarboxylic acid ester Thiocarboxylic acid or derivatives Solid logp 1.12 ALOGPS logs -2.52 ALOGPS solubility 2.84e+00 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 0.82 ChemAxon pka_strongest_basic 4.01 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(undecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid ChemAxon average_mass 935.81 ChemAxon mono_mass 935.266623627 ChemAxon smiles CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N ChemAxon formula C32H56N7O17P3S ChemAxon inchi InChI=1S/C32H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-23(41)60-16-15-34-22(40)13-14-35-30(44)27(43)32(2,3)18-53-59(50,51)56-58(48,49)52-17-21-26(55-57(45,46)47)25(42)31(54-21)39-20-38-24-28(33)36-19-37-29(24)39/h19-21,25-27,31,42-43H,4-18H2,1-3H3,(H,34,40)(H,35,44)(H,48,49)(H,50,51)(H2,33,36,37)(H2,45,46,47)/t21-,25-,26-,27?,31-/m1/s1 ChemAxon inchikey IZWCGXGZGYKDHR-WMMBNDHFSA-N ChemAxon polar_surface_area 363.63 ChemAxon refractivity 213.64 ChemAxon polarizability 89.35 ChemAxon rotatable_bond_count 29 ChemAxon acceptor_count 17 ChemAxon donor_count 9 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 3077 Specdb::NmrOneD 152150 Specdb::NmrOneD 152151 Specdb::NmrOneD 152152 Specdb::NmrOneD 152153 Specdb::NmrOneD 152154 Specdb::NmrOneD 152155 Specdb::NmrOneD 152156 Specdb::NmrOneD 152157 Specdb::NmrOneD 152158 Specdb::NmrOneD 152159 Specdb::NmrOneD 152160 Specdb::NmrOneD 152161 Specdb::NmrOneD 152162 Specdb::NmrOneD 152163 Specdb::NmrOneD 152164 Specdb::NmrOneD 152165 Specdb::NmrOneD 152166 Specdb::NmrOneD 152167 Specdb::NmrOneD 152168 Specdb::NmrOneD 152169 Specdb::MsMs 292114 Specdb::MsMs 292115 Specdb::MsMs 292116 Specdb::MsMs 332218 Specdb::MsMs 332219 Specdb::MsMs 332220 Specdb::MsMs 2809283 Specdb::MsMs 2809284 Specdb::MsMs 2809285 Specdb::MsMs 2900451 Specdb::MsMs 2900452 Specdb::MsMs 2900453 HMDB13114 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha Q99943 AGPAT1 1-acyl-sn-glycerol-3-phosphate acyltransferase beta O15120 AGPAT2 1-acyl-sn-glycerol-3-phosphate acyltransferase delta Q9NRZ5 AGPAT4 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon Q9NUQ2 AGPAT5 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma Q9NRZ7 AGPAT3 2-acylglycerol O-acyltransferase 1 Q96PD6 MOGAT1 2-acylglycerol O-acyltransferase 2 Q3SYC2 MOGAT2 2-acylglycerol O-acyltransferase 3 Q86VF5 MOGAT3 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial P21953 BCKDHB 3-ketoacyl-CoA thiolase, mitochondrial P42765 ACAA2 3-ketoacyl-CoA thiolase, peroxisomal P09110 ACAA1 Acyl-CoA dehydrogenase family member 10 Q6JQN1 ACAD10 Acyl-CoA dehydrogenase family member 11 Q709F0 ACAD11 Acyl-CoA synthetase family member 2, mitochondrial Q96CM8 ACSF2 Acyl-CoA synthetase family member 3, mitochondrial Q4G176 ACSF3 Acyl-CoA synthetase family member 4 Q4L235 AASDH Acyl-CoA wax alcohol acyltransferase 1 Q58HT5 AWAT1 Acyl-CoA wax alcohol acyltransferase 2 Q6E213 AWAT2 Acyl-CoA-binding protein P07108 DBI Acyl-coenzyme A thioesterase 1 Q86TX2 ACOT1 Acyl-coenzyme A thioesterase 11 Q8WXI4 ACOT11 Acyl-coenzyme A thioesterase 2, mitochondrial P49753 ACOT2 Acyl-coenzyme A thioesterase 4 Q8N9L9 ACOT4 Acyl-coenzyme A thioesterase 8 O14734 ACOT8 Acyl-coenzyme A thioesterase 9, mitochondrial Q9Y305 ACOT9 Bile acid-CoA:amino acid N-acyltransferase Q14032 BAAT Bile acyl-CoA synthetase Q9Y2P5 SLC27A5 Cytosolic acyl coenzyme A thioester hydrolase O00154 ACOT7 Cytosolic acyl coenzyme A thioester hydrolase-like Q6ZUV0 ACOT7L Diacylglycerol O-acyltransferase 1 O75907 DGAT1 Diacylglycerol O-acyltransferase 2 Q96PD7 DGAT2 Diacylglycerol O-acyltransferase 2-like protein 6 Q6ZPD8 DGAT2L6 Dihydroxyacetone phosphate acyltransferase O15228 GNPAT Enoyl-CoA delta isomerase 2, mitochondrial O75521 ECI2 Fatty acid-binding protein, heart P05413 FABP3 Fatty acyl-CoA reductase 1 Q8WVX9 FAR1 Fatty acyl-CoA reductase 2 Q96K12 FAR2 Glycerol-3-phosphate acyltransferase 1, mitochondrial Q9HCL2 GPAM Glycerol-3-phosphate acyltransferase 2, mitochondrial Q6NUI2 GPAT2 Glycerol-3-phosphate acyltransferase 3 Q53EU6 AGPAT9 Glycerol-3-phosphate acyltransferase 4 Q86UL3 AGPAT6 Glycine N-acyltransferase Q6IB77 GLYAT Glycine N-acyltransferase-like protein 1 Q969I3 GLYATL1 Glycine N-acyltransferase-like protein 2 Q8WU03 GLYATL2 Hepatic triacylglycerol lipase P11150 LIPC Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial P11182 DBT Long-chain fatty acid transport protein 3 Q5K4L6 SLC27A3 Long-chain fatty acid transport protein 4 Q6P1M0 SLC27A4 Long-chain-fatty-acid--CoA ligase ACSBG1 Q96GR2 ACSBG1 Long-chain-fatty-acid--CoA ligase ACSBG2 Q5FVE4 ACSBG2 Lysocardiolipin acyltransferase 1 Q6UWP7 LCLAT1 Lysophospholipid acyltransferase 5 Q6P1A2 LPCAT3 Lysophospholipid acyltransferase LPCAT4 Q643R3 LPCAT4 Nef-associated protein 1 Q9BU70 C9orf156 Peroxisomal trans-2-enoyl-CoA reductase Q9BY49 PECR Peroxisome proliferator-activated receptor alpha Q07869 PPARA Peroxisome proliferator-activated receptor delta Q03181 PPARD Peroxisome proliferator-activated receptor gamma P37231 PPARG Putative diacylglycerol O-acyltransferase 2-like protein 7 Q6IED9 DGAT2L7 Sterol O-acyltransferase 1 P35610 SOAT1 Sterol O-acyltransferase 2 O75908 SOAT2 Trifunctional enzyme subunit beta, mitochondrial P55084 HADHB Very long-chain acyl-CoA synthetase O14975 SLC27A2