Record Information
Version2.0
Creation Date2012-05-31 14:20:52 -0600
Update Date2015-06-03 17:19:02 -0600
Secondary Accession Numbers
  • ECMDB12184
Identification
Name:Adenosyl cobinamide phosphate
DescriptionAdenosyl cobinamide phosphate, a known intermediate of the de novo biosynthetic pathway, is involved in Porphyrin and chlorophyll metabolism.In Salmonella typhimurium LT2, under anaerobic conditions, CobU (EC 2.7.7.62 and EC 2.7.1.156), CobT (EC 2.4.2.21), CobC (EC 3.1.3.73) and CobS (EC 2.7.8.26) catalyse reactions in the nucleotide loop
Structure
Thumb
Synonyms:
  • Adenosyl cobinamide phosphoric acid
  • Adenosylcobinamide-P
Chemical Formula:C58H85CoN16O14P
Weight:Average: 1320.3013
Monoisotopic: 1319.550078214
InChI Key:MQCMBMUJJHSGIF-QMUWONGRSA-M
InChI:InChI=1S/C48H74N11O11P.C10H12N5O3.Co/c1-23(70-71(67,68)69)22-55-38(66)16-17-45(6)29(18-35(52)63)43-48(9)47(8,21-37(54)65)28(12-15-34(51)62)40(59-48)25(3)42-46(7,20-36(53)64)26(10-13-32(49)60)30(56-42)19-31-44(4,5)27(11-14-33(50)61)39(57-31)24(2)41(45)58-43;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h19,23,26-29,43H,10-18,20-22H2,1-9H3,(H16,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63,64,65,66,67,68,69);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,26-,27-,28-,29+,43-,45-,46+,47+,48+;4-,6-,7-,10-;/m11./s1
CAS number:Not Available
IUPAC Name:(3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide
Traditional IUPAC Name:(3R,4S,5S,9S,10S,15S,19R,20R,21R)-1-{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-5,10,15-tris(2-carbamoylethyl)-4,9,20-tris(carbamoylmethyl)-3,4,7,9,14,14,17,19-octamethyl-19-(2-{[(2R)-2-(phosphonooxy)propyl]carbamoyl}ethyl)-2lambda5,22,23lambda5,24lambda5-tetraaza-1-cobaltaoctacyclo[11.9.1.1^{1,8}.0^{2,6}.0^{3,21}.0^{16,23}.0^{18,22}.0^{11,24}]tetracosa-2(6),7,11(24),12,16(23),17-hexaene-2,23,24-tris(ylium)-1,1-diuide
SMILES:C[C@H](CNC(=O)CC[C@]1(C)[C@@H](CC(=O)N)[C@@]2([H])N([Co+]C[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=CN=C4N)\C1=C(C)/C1=N/C(=C\C3=N\C(=C(C)/C4=N[C@]2(C)[C@@](C)(CC(=O)N)[C@@H]4CCC(=O)N)\[C@@](C)(CC(=O)N)[C@@H]3CCC(=O)N)/C(C)(C)[C@@H]1CCC(=O)N)OP(=O)(O)O
Chemical Taxonomy
Description belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Phosphoethanolamine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Alkyl phosphate
  • Monosaccharide
  • Fatty amide
  • Fatty acyl
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Pyrrolidine
  • Tetrahydrofuran
  • Pyrroline
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • 1,2-diol
  • Azacycle
  • Oxacycle
  • Organic metal salt
  • Carboxylic acid derivative
  • Organic transition metal salt
  • Metalloheterocycle
  • Organometallic compound
  • Organic transition metal moeity
  • Organonitrogen compound
  • Transition metal alkyl
  • Organic salt
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Primary amine
  • Organic oxide
  • Alcohol
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP-0.04ALOGPS
logP-14ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area485.98 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity330.2 m³·mol⁻¹ChemAxon
Polarizability131.82 ųChemAxon
Number of Rings11ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-1492000000-cd3da96c47e731cd382eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1951000000-6afc304e19ecce421bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-3930000000-a2544aa4be58bc1ea4f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0089000000-e18b5ef096db2972b93eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h99-0981000000-a66bdec455b06e994738View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1910000000-2c6dbf19ff223f6e331aView in MoNA
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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID2481
HMDB IDHMDB12184
Pubchem Compound ID23724501
Kegg IDC06509
ChemSpider ID21864728
Wikipedia IDNot Available
BioCyc IDADENOSYLCOBINAMIDE-P
EcoCyc IDADENOSYLCOBINAMIDE-P

Enzymes

General function:
Involved in nucleotide binding
Specific function:
ATP-dependent phosphorylation of adenosylcobinamide and adds GMP to adenosylcobinamide phosphate
Gene Name:
cobU
Uniprot ID:
P0AE76
Molecular weight:
20164
Reactions
ATP or GTP + adenosylcobinamide = adenosylcobinamide phosphate + ADP or GDP.
GTP + adenosylcobinamide phosphate = diphosphate + adenosylcobinamide-GDP.