(3S)-Citryl-CoA (ECMDB23162) (M2MDB003552)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (8)
Record Information
Version2.0
Creation Date2012-10-10 12:19:50 -0600
Update Date2015-06-04 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
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
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-hydroxybutanedioateGenerator
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-hydroxybutanedioateGenerator
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 acidGenerator
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.6 g/LALOGPS
logP-0.64ALOGPS
logP-3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area465.44 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity196.23 m³·mol⁻¹ChemAxon
Polarizability81.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0944000224-9542d959256d3cd045a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0934100000-5b84d8dda3d4cee931b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2932000000-6b0d383bd22a5fa40bcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3901010242-13473c4f022d7d0702aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900110001-8c24a7f0e664b2f57836View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-83ecd668f8a6a2a958d3View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID439266
Kegg IDC00566
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Citrate lyase subunit beta
General function:
Involved in carbon-carbon lyase activity
Specific function:
Represents a citryl-ACP lyase
Gene Name:
citE
Uniprot ID:
P0A9I1
Molecular weight:
33109
Reactions
Citrate = acetate + oxaloacetate.
(3S)-citryl-CoA = acetyl-CoA + oxaloacetate.
Protein Details
2. Citrate lyase alpha chain
General function:
Involved in citrate CoA-transferase activity
Specific function:
Represents a citrate:acetyl-ACP transferase
Gene Name:
citF
Uniprot ID:
P75726
Molecular weight:
55172
Reactions
Citrate = acetate + oxaloacetate.
Acetyl-CoA + citrate = acetate + (3S)-citryl-CoA.