3'-dephospho-CoA (PAMDB003559)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003559
Identification
Name: 3'-dephospho-CoA
Description:3'-dephospho-CoA is a substrate for the enzyme 2-(5''-triphosphoribosyl)-3'-dephosphocoenzyme-A synthase (CitG), which catalyzes the formation of 2-(5''-triphosphoribosyl)-3'-dephosphocoenzyme-A, the precursor of the prosthetic group of the holo-acyl carrier protein (gamma chain) of citrate lyase, from ATP and dephospho-CoA. The reaction is: ATP + 3-dephospho-CoA = 2'-(5-triphosphoribosyl)-3'-dephospho-CoA + adenine. The gamma-subunit of citrate lyase (EC 4.1.3.6) contains the prosthetic group 2'-(5"-phosphoribosyl)-3'-dephospho-CoA and serves as an acyl carrier protein (ACP) in Pseudomonas aeruginosa. It has been shown that in Pseudomonas aeruginosa the proteins CitG and CitX are essential for holo-ACP synthesis and that CitG catalyzes the conversion of ATP and dephospho-CoA to adenine and 2'-(5"-triphosphoribosyl)-3'-dephospho-CoA [PMID:11042274]
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulfanylethyl)aminopropyl}amino)butyl dihydrogen diphosphate (non-preferred name)
  • (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulfanylethyl)aminopropyl}amino)butyl dihydrogen diphosphoric acid (non-preferred name)
  • (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulphanylethyl)aminopropyl}amino)butyl dihydrogen diphosphate (non-preferred name)
  • (2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-3,4-dihydroxytetrahydro-2-furanylmethyl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-(2-sulphanylethyl)aminopropyl}amino)butyl dihydrogen diphosphoric acid (non-preferred name)
  • (2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulfanylethylamino)propylaminobutyl hydrogen phosphate
  • (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulfanylethylamino)propylaminobutyl hydrogen phosphoric acid
  • (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulphanylethylamino)propylaminobutyl hydrogen phosphate
  • (2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-ylmethoxy-hydroxyphosphoryl (3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-3-oxo-3-(2-sulphanylethylamino)propylaminobutyl hydrogen phosphoric acid
  • 3'-Dephospho-CoA
  • 3'-dephospho-Coenzyme A
  • 3'-O-dephosphono-CoA
  • 3'-O-dephosphono-Coenzyme A
  • 3-dephospho-CoA
  • Dephospho-CoA
  • Dephospho-Coenzyme A
  • Dephosphocoenzyme A
Chemical Formula: C21H35N7O13P2S
Average Molecular Weight: 687.554
Monoisotopic Molecular Weight: 687.148877955
InChI Key: KDTSHFARGAKYJN-IBOSZNHHSA-N
InChI:InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16+,20-/m1/s1
CAS number: 3633-59-8
IUPAC Name:[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid
Traditional IUPAC Name: 3'-dephospho-coa
SMILES:CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Alkylthiol
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.56 mg/mLALOGPS
logP-0.98ALOGPS
logP-5.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.03 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity151.87 m3·mol-1ChemAxon
Polarizability63.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + pantotheine 4'-phosphate > Pyrophosphate + 3'-dephospho-CoA
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2930102000-19d2796dee5d14788e39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3930000000-d4541feacee9a6c7a4e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4900000000-1307cbce80b215d981b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0040-2910618000-58e100b1447a771ecd7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1910200000-ba57f132dee9798389faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-3900000000-d382c7ac6874be7ea151View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15468
HMDB IDHMDB01373
Pubchem Compound ID439335
Kegg IDC00882
ChemSpider ID392407
Wikipedia IDNot Available
BioCyc IDDEPHOSPHO-COA
EcoCyc IDDEPHOSPHO-COA
Ligand ExpoCOD