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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001083
Secondary Accession Numbers
  • HMDB01083
Metabolite Identification
Common NameAdenosyl cobyrinic acid a,c diamide
DescriptionAdenosyl cobyrinic acid a,c diamide, also known as adenosylcob(iii)yrinate a,c-diamide, belongs to the class of organic compounds known as precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring. A cobalt corrinoid that is cob(III)yrinic acid a,c-diamide having a 5'-adenosyl group attached to the central cobalt atom. Adenosyl cobyrinic acid a,c diamide is a very strong basic compound (based on its pKa). Adenosyl cobyrinic acid a,c diamide exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752175
Synonyms
ValueSource
Adenosyl cobyrinate a,c diamideChEBI
Adenosyl cobyrinate diamideChEBI
Adenosylcobyrinic acid a,c-diamideChEBI
Adenosyl cobyrinic acid diamideGenerator
Adenosylcobyrinate a,c-diamideGenerator
Adenosylcob(III)yrinate a,c-diamideHMDB
Adenosyl cobyrinic acid a,c diamideGenerator
Chemical FormulaC55H73CoN11O15
Average Molecular Weight1187.166
Monoisotopic Molecular Weight1186.461960915
IUPAC Name{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,6Z,8S,9S,11Z,14S,18R,19R)-3,8-bis(carbamoylmethyl)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
Traditional Name{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,6Z,8S,9S,11Z,14S,18R,19R)-3,8-bis(carbamoylmethyl)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium
CAS Registry NumberNot Available
SMILES
[H][C@]12[C@H](CC(O)=O)[C@@](C)(CCC(O)=O)\C(N1[Co+]C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)=C(C)\C1=N\C(=C/C3=N/C(=C(C)\C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(O)=O)/[C@@](C)(CC(N)=O)[C@@H]3CCC(O)=O)\C(C)(C)[C@@H]1CCC(O)=O
InChI Identifier
InChI=1S/C45H62N6O12.C10H12N5O3.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;/h18,23-26,40H,9-17,19-20H2,1-8H3,(H10,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,24-,25-,26+,40-,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1
InChI KeyOCNLJCZKGHKJGF-NQYRMHKHSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassCorrinoids
Direct ParentPrecorrins
Alternative Parents
Substituents
  • Precorrin
  • Metallotetrapyrrole skeleton
  • Pentacarboxylic acid or derivatives
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Fatty amide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Fatty acyl
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Pyrroline
  • Pyrrolidine
  • Azole
  • Ketimine
  • Secondary alcohol
  • 1,2-diol
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Carbene-type 1,3-dipolar compound
  • Carboxylic acid
  • Organic transition metal salt
  • Organic cobalt salt
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Imine
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Alcohol
  • Organic salt
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP0.57ALOGPS
logP-9.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)8.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area432.31 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity288.98 m³·mol⁻¹ChemAxon
Polarizability118.72 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+358.52932859911
AllCCS[M-H]-159.46732859911
AllCCS[M+H]+358.532859911
AllCCS[M+H-H2O]+358.632859911
AllCCS[M+NH4]+358.432859911
AllCCS[M+Na]+358.432859911
AllCCS[M-H]-159.532859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-170.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenosyl cobyrinic acid a,c diamide 10V, Positive-QTOFsplash10-05r9-0900000000-37f9ab56be98a89bca3a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenosyl cobyrinic acid a,c diamide 20V, Positive-QTOFsplash10-000i-0900000000-23bae7a37fc3586809182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adenosyl cobyrinic acid a,c diamide 40V, Positive-QTOFsplash10-0a4i-7900000000-6d2d938d578f9e7a6d912021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022414
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID2482
Food Biomarker OntologyNot Available
VMH IDADCOBDAM
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
Reactions
Cob(I)yrinate a,c diamide + Adenosine triphosphate → Adenosyl cobyrinic acid a,c diamide + Triphosphatedetails