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Record Information
Version	2.0
Creation Date	2012-10-10 12:19:50 -0600
Update Date	2015-06-04 16:20:32 -0600
Secondary Accession Numbers	ECMDB23162
Identification
Name:	(3S)-Citryl-CoA
Description	(3S)-Citryl-CoA is an (S)-3-hydroxyacyl-CoA having (3S)-citryl as the S-acyl group. It is a substrate for the enzyme citryl-CoA lyase (EC 4.1.3.34), an enzyme that catalyzes the chemical reaction (3S)-citryl-CoA <=> acetyl-CoA + oxaloacetate
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae0894c8> Close
Synonyms:	Value Source 2-[2-({2-[(3-{[4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoethyl]-2-hydroxybutanedioate Generator 2-[2-({2-[(3-{[4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-oxoethyl]-2-hydroxybutanedioate Generator 2-[2-({2-[(3-{[4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-2-oxoethyl]-2-hydroxybutanedioic acid Generator
Chemical Formula:	C27H42N7O22P3S
Weight:	Average: 941.642 Monoisotopic: 941.131646289
InChI Key:	IHVFHZGGMJDGGZ-CLSGQFMISA-N
InChI:	InChI=1S/C27H42N7O22P3S/c1-26(2,20(40)23(41)30-4-3-14(35)29-5-6-60-16(38)8-27(44,25(42)43)7-15(36)37)10-53-59(50,51)56-58(48,49)52-9-13-19(55-57(45,46)47)18(39)24(54-13)34-12-33-17-21(28)31-11-32-22(17)34/h11-13,18-20,24,39-40,44H,3-10H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,42,43)(H,48,49)(H,50,51)(H2,28,31,32)(H2,45,46,47)/t13-,18-,19-,20?,24-,27?/m1/s1
CAS number:	Not Available
IUPAC Name:	2-[2-({2-[(3-{[4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-2-oxoethyl]-2-hydroxybutanedioic acid
Traditional IUPAC Name:	(3S)-citryl-coa
SMILES:	[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)CC(O)(CC(O)=O)C(O)=O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty acyl thioesters
Direct Parent	Acyl CoAs
Alternative Parents	Coenzyme A and derivatives Purine ribonucleoside diphosphates Ribonucleoside 3'-phosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates 1,3-dicarbonyl compounds Imidolactams N-acyl amines N-substituted imidazoles Methyl esters Heteroaromatic compounds Tetrahydrofurans Thioesters Secondary alcohols Secondary carboxylic acid amides Carbothioic S-esters Oxacyclic compounds Monocarboxylic acids and derivatives Sulfenyl compounds Azacyclic compounds Primary amines Hydrocarbon derivatives Organic oxides Organopnictogen compounds
Substituents	Coenzyme a or derivatives Purine ribonucleoside 3',5'-bisphosphate Purine ribonucleoside bisphosphate Purine ribonucleoside diphosphate Ribonucleoside 3'-phosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Monosaccharide phosphate Organic pyrophosphate Pentose monosaccharide Imidazopyrimidine Purine Aminopyrimidine Monoalkyl phosphate Organic phosphoric acid derivative N-substituted imidazole N-acyl-amine Phosphoric acid ester Monosaccharide Alkyl phosphate Imidolactam Pyrimidine 1,3-dicarbonyl compound Fatty amide Imidazole Azole Heteroaromatic compound Tetrahydrofuran Methyl ester Carbothioic s-ester Thiocarboxylic acid ester Secondary carboxylic acid amide Secondary alcohol Carboxamide group Carboxylic acid ester Amino acid or derivatives Thiocarboxylic acid or derivatives Sulfenyl compound Carboxylic acid derivative Organoheterocyclic compound Azacycle Oxacycle Monocarboxylic acid or derivatives Organic oxygen compound Amine Organonitrogen compound Carbonyl group Organic nitrogen compound Organosulfur compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organooxygen compound Primary amine Alcohol Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-5
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.6 g/L ALOGPS logP -0.64 ALOGPS logP -3 ChemAxon logS -2.2 ALOGPS pKa (Strongest Acidic) 0.82 ChemAxon Physiological Charge -5 ChemAxon Hydrogen Acceptor Count 24 ChemAxon Hydrogen Donor Count 12 ChemAxon Polar Surface Area 465.44 Ų ChemAxon Rotatable Bond Count 25 ChemAxon Refractivity 196.23 m³·mol⁻¹ ChemAxon Polarizability 81.66 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Acetyl-CoA + Citric acid > Acetic acid + (3S)-Citryl-CoA (3S)-Citryl-CoA > Acetyl-CoA + Oxalacetic acid Acetyl-CoA + Citric acid <> Acetic acid + (3S)-Citryl-CoA (3S)-Citryl-CoA <> Acetyl-CoA + Oxalacetic acid
SMPDB Pathways:	Not Available
KEGG Pathways:	Citrate cycle (TCA cycle) ec00020 Two-component system ec02020
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0079-0944000224-9542d959256d3cd045a9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0934100000-5b84d8dda3d4cee931b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-2932000000-6b0d383bd22a5fa40bcb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-003r-3901010242-13473c4f022d7d0702ae View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-3900110001-8c24a7f0e664b2f57836 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-057i-5900100000-83ecd668f8a6a2a958d3 View in MoNA MS Mass Spectrum (Electron Ionization) Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 439266 Kegg ID C00566 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes