Adenosylcob(III)yrinic acid a,c-diamide (ECMDB23132) (M2MDB003522)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-10-10 12:18:06 -0600
Update Date2015-10-02 02:25:54 -0600
Secondary Accession Numbers
  • ECMDB23132
Identification
Name:Adenosylcob(III)yrinic acid a,c-diamide
DescriptionMost prokaryotic organisms as well as animals (including human) and protists have enzyme that require adenosylcobalamin as cofactor, whereas plants and fungi are thought not to use it. It is one of the most structurally complex protein cofactors ans its biosynthesis remains one of the most enigmatic and exigent metabolic pathways in nature, requiring around 30 enzymes. Two distinct yet similar routes exist, known as the oxygene-dependent (aerobic route) and oxygen-independent (anaerobic route) pathways. These pathways diverge at precorrin-2 and merge again at adenosylcobyrate. The major difference between these two routes include the timing of cobalt insertion, the requirement for oxygen and the nature of the extruded carbon fragment which is lost during the ring construction process.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • Adenosylcob(iii)yrinate a,c-diamide
Chemical Formula:C55H75CoN11O15
Weight:Average: 1189.1819
Monoisotopic: 1188.477610979
InChI Key:MEXRZHASDDAAJB-QOCQOLRHSA-N
InChI:InChI=1S/C45H62N6O12.C10H13N5O3.Co/c1-21-36-24(10-13-32(56)57)41(3,4)28(49-36)18-27-23(9-12-31(54)55)43(6,19-29(46)52)39(48-27)22(2)37-25(11-14-33(58)59)44(7,20-30(47)53)45(8,51-37)40-26(17-35(62)63)42(5,38(21)50-40)16-15-34(60)61;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h18,23-26,40,51H,9-17,19-20H2,1-8H3,(H2,46,52)(H2,47,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)(H,62,63);2-4,6-7,10,16-17H,1H3,(H2,11,12,13);/q;;+3/t23-,24-,25-,26+,40?,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1
CAS number:Not Available
IUPAC Name:cobalt(3+) ion (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol 3-[(2R,3S,4S,8S,9S,14S,18R,19R)-4,14,18-tris(2-carboxyethyl)-19-(carboxymethyl)-3,8-bis(C-hydroxycarbonimidoylmethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5,7(22),10,12(21),15,17(20)-hexaen-9-yl]propanoic acid
Traditional IUPAC Name:cobalt(3+) ion 3-[(2R,3S,4S,8S,9S,14S,18R,19R)-4,14,18-tris(2-carboxyethyl)-19-(carboxymethyl)-3,8-bis(C-hydroxycarbonimidoylmethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1²,⁵.1⁷,¹⁰.1¹²,¹⁵]tricosa-5,7(22),10,12(21),15,17(20)-hexaen-9-yl]propanoic acid 5'-deoxyadenosine
SMILES:[Co+3].[H][C@]1(C)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O.[H][C@@]1(CCC(O)=O)C2=CC3=NC(=C(C)C4=NC([H])([C@]([H])(CC(O)=O)[C@@]4(C)CCC(O)=O)[C@]4(C)NC(=C(C)C(=N2)[C@@]1(C)CC(O)=N)[C@@]([H])(CCC(O)=O)[C@]4(C)CC(O)=N)[C@@]([H])(CCC(O)=O)C3(C)C
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
  • N-glycosyl compound
  • Glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Pyrroline
  • Pyrrolidine
  • Imidazole
  • Azole
  • Secondary alcohol
  • Ketimine
  • Oxacycle
  • Azacycle
  • Organic transition metal salt
  • Secondary amine
  • Enamine
  • Secondary aliphatic amine
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic cobalt salt
  • Organic salt
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP0.88ChemAxon
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)8.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area323.77 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity251.16 m³·mol⁻¹ChemAxon
Polarizability91.96 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Cob(I)yrinate a,c diamide > Triphosphate + Adenosylcob(III)yrinic acid a,c-diamide
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Cob(I)yrinic acid a,c-diamide adenosyltransferase
General function:
Involved in ATP binding
Specific function:
Required for both de novo synthesis of the corrin ring for the assimilation of exogenous corrinoids. Participates in the adenosylation of a variety of incomplete and complete corrinoids
Gene Name:
btuR
Uniprot ID:
P0A9H5
Molecular weight:
21999
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.
Protein Details
2. Ethanolamine utilization cobalamin adenosyltransferase
General function:
Involved in ATP binding
Specific function:
Converts CNB12 to ADOB12
Gene Name:
eutT
Uniprot ID:
P65643
Molecular weight:
30171
Reactions
ATP + cob(I)yrinic acid a,c-diamide = triphosphate + adenosylcob(III)yrinic acid a,c-diamide.
ATP + cobinamide = triphosphate + adenosylcobinamide.